Let Love Keep Us Together
by TheDisneyOutsider
Summary: Sequel to 'Love Will Keep Us Together.' Luke and Lorelai adjust to Jess and Rory becoming teenagers and the challenges that come with it as they settle into life as a family.
1. Chapter 1

**A/N- This is the sequel story to Love Will Keep Us Together. If you haven't read that story yet I suggest you head on over there first!**

* * *

March 19th 1999

"Jess don't you think that even if I believed it was a day off school that I might notice the school is still open when I look over from the diner, across the street from said school, and see all the students heading into the building?" Luke spoke with ease as he fried eggs on the stove, used to his nephew's antics by now.

Jess shrugged, "Some people are just overachievers Uncle Luke, what can I say."

Luke gave the teen a blank stare, "Go get ready for school."

With an eye roll, the teen accepted his defeat and turned on his heels to exit the small kitchen.

"I told you it wouldn't work," Rory gloated as she passed him through the kitchen door and the boy made a face at his step-sister.

"Yeah well if you would have agreed to back me up on the matter it would have!" he yelled through the house as he headed into his room to reluctantly grab his books.

His room was bigger than Rory's, extending the house to add a bit more space had given the family the ability to make it a decent size, and though the parents had made sure that Rory hadn't been jealous of the fact, she had assured them that she was just fine with her smaller room if it meant that they got to stay living in the girls' old house. His room was still on the first floor, however, right next to the staircase in the living room, making the upstairs a private, 'kid-free', retreat for the couple of the house. The biggest thrill for Jess had been actually having a door and four walls to call his own. Not that he hadn't gotten used to the lack of privacy, sharing the tight quarters of the apartment with Luke for over a year, but the older Jess was getting, the more he appreciated their relocation.

Living with the girls hadn't taken much adjustment in the end. Sure it was a little odd not living in the apartment at first. For a while Jess actually kind of missed it and would hide out up there while Luke worked down in the diner. But really, the family had already been spending so much time at the Gilmore house that moving in full-time hadn't felt that different. The boys had long since passed the feeling of being guests in the home and everyone took on their new family role pretty well.

"Jess get your butt out here if you want a ride from me!" Lorelai shouted through the house unnecessarily. She was only in the living room and Jess hadn't shut his door.

Standing in his doorway, still readjusting the watch on his arm, Jess answered the woman, who was now standing near the door with Rory in tow, waiting to leave, "We'll walk today," he spoke for both teens, even though Rory looked every bit ready to accept the ride.

"You'll walk?" Lorelai asked in disbelief, "I'm sorry, is this coming from the same boy who complains on a daily basis that his legs couldn't possibly make the incredibly LONG walk all the way to school?"

"Well it's true we're no longer living in the stone ages like you grew up in Lorelai, usually I'd agree we shouldn't be made to walk _all_ the way to school, uphill in a snowstorm, but yes, on this particular day I think a walk might do us some good, you wouldn't want us getting lazy now would you?"

Lorelai shook her head in astonishment, too tired to think of one of her regular witty comebacks, "Sometimes I really can't keep up with how your brain works kid. Okay, well if you're going to walk you two better get a move on, it's twenty minutes to."

Jess nodded once, bypassing the woman at the door while grabbing Rory's arm to drag her with him. The boy turned, heading the long way to school, but Rory didn't question it, like her mother she had long ago stopped trying to figure Jess out. Sometimes he liked to walk the less populated route to school anyway, less time wasted interacting with the idiots that inhabited their school he once explained.

They walked relatively quietly through the cleared path of the woods, not unusual for either of the teens on a school morning, both liking the quiet time before a long day of school interactions.

Rory only spoke up when she noticed her brother veering away from her and the direction of the high school, "Where are you going?"

"Social studies with Fritz first period," Jess shrugged nonchalant, "Don't feel like sitting through that wack's class today."

"Jess you can't skip again!" The girl chastised wide-eyed, "It was too close of a call last time and I'm done covering for you!"

"I won't get caught," the teen insisted with an eye roll, "you won't have to cover anything. Don't worry, it's not like I'm asking you to come with me, Miss Harvard."

"Come on Jess, just come to school! You've already scored way lower than you should have on two tests in that class, not to mention the others, Luke and Mom are going to start catching on eventually, and you're ruining your GPA!"

"Rory, I'm fine! Seriously stop worrying about me, I'm only skipping first period anyway. I've got it covered. I'll even study with you later if it'll make you happy."

"You know you're probably smarter than me if you actually took your school work seriously every once in a while, you could be trying out for Chilton with me," Rory pointed out, "Wouldn't you like to stay together?"

"We've already discussed this Ror, Harvard's your thing, besides we don't even know if you'll get into Chilton."

"Gee thanks for the confidence boost," Rory muttered.

"That's not what I meant and you know it."

Rory sighed, "I know, it's just we've been in the same class since you moved here. It's going to be weird if we're not."

Jess nodded, fixing her with a reassuring look, "Well we don't have to worry about it right now anyway, right? Now you better hurry or you're going to be late."

"Come on Jess, just come to school! Why do you insist on making your life so much harder?"

Jess just shrugged, trademark smirk on his face, "Because following the rules all the time is boring."

"Ugh! You're impossible sometimes, you know that?"

"Love you too," Jess laughed, turning towards the bridge.

The old bridge hadn't changed much in the years Jess had been visiting it. It was still quiet, still peaceful and Jess was still grateful that no matter how much had changed in his life, he could always count on it to be there, just like his bench in New York.

Luke and Jess had actually visited his old stomping ground last summer, a weekend when the girls were off on a pampering day with Sookie and Luke had needed to grab some material from the 'Big Apple' as Rory still loved to call it if not only to aggravate Jess. It was the first time Jess had been back since he was sent away when he was eleven and he felt somewhat relieved to see that not much had changed in the four years he had missed it. It did, however, seem even busier than when Jess had left, if that was possible, although he wasn't sure if that was actually true or more due to the fact that Jess had spent the last four years in a community the size of a fishbowl. Maybe he had really become a small town boy after all.

Thinking back, it almost amazed him that he, a five, eight, ten-year-old had walked these busy streets alone, at night even. It was almost a wonder that he had made it to Stars Hollow in one piece.

Jess had returned from that trip with a new appreciation for the town he now called home. New York would always have a piece of his heart of course, but he had learned over the years that small towns weren't so bad after all.

He sat down on the old bridge, the wood weathered down from years of exposure to the elements, and pulled out his book, checking his watch quickly to be sure he would make it back in time for his next class. Jess may have liked to bend the rules a bit when he could, but he also knew how far those rules could be bent before he really got in trouble. He wasn't planning on getting caught, having done this a few times had made him better at the ins and outs of ditching, but he also knew that if he did, explaining one missed class to Luke as opposed to a full day, would be a lot easier.

* * *

Luke grabbed his keys off the table by the door as he left the house, being sure to lock the door behind him before heading towards his truck. It was unusual for him to be the last one to leave the house in the morning. Usually, Luke liked to be at the diner to help open up early. He had been trying as of late, however, to lessen his daily duties, passing them down to his staff instead, in order to be able to spend more time at home with his family. With both parents working full-time jobs the lack of family time had been becoming an increasing issue. Lorelai didn't have as much control over her duties, not being the owner of the Inn after all, so Luke took it upon himself to lessen his load the best he could in order to give the family with two rapidly growing teens some much needed time together.

Luke still couldn't believe that Jess had turned fifteen last Sunday, Rory soon following him in the fall. It didn't seem like all that long ago that the house was home to two children when suddenly it felt like Luke blinked and the kids were practically grown. Okay, well maybe not grown per se, but they were definitely growing into their role as teenagers, a fact Luke was still trying to grow accustomed to.

He was glad to have Lorelai by his side through it all though. Sure he would have found a way to do it on his own. Jess was usually a pretty good kid, they both were, but still, the peace of mind to know that he wasn't in it completely alone anymore was a huge weight off his shoulders, no matter how much he still managed to worry about his boy.

Both parents had taken on the role as step-parents to each other's kid incredibly naturally. There was no real feeling of my kid, your kid, anymore in the house and both teens knew that neither adult was more in charge than the other. The family really had moulded together exceedingly well. They had a good routine now, like a well-oiled machine.

Luke greeted his staff as he entered the diner. Caesar now being his second in command, in charge when Luke was out, and Luke had hired a few new employees to help pick up the slack on those occasions as well. Jess too had started working there a few hours on Tuesdays and Thursdays after school and every second Saturday. Luke had started him off slow, considering he was not only still technically too young to legally be working there, but also because Luke didn't want it to interfere with the boy's school work. At first, Luke had been very hesitant to agree to it at all, even to as few hours as he was currently giving Jess, but Jess had long since grown out of the dollar discipline system that Luke had put in place when the boy was younger, and after near constant begging from the younger boy, he realized it was about time that the kid started earning some real money for himself. Luke reasoned that if he wanted a job that badly at least it would be under his uncle's careful watch.

Rory, who was much more dedicated to her schoolwork, helped her mom out at the Inn when she could, but her worries were less about making money and more to do with getting into Harvard. The family had been talking about her applying to get into Chilton, a school that could apparently prepare her much better than Stars Hollow High for having the greatest chance at making her college dreams come true according to her principal. Luke had no doubt that she would be accepted as soon as the fall semester, he only hoped they would be able to find the money for it when she did.

The man sighed as he prepared himself for another day. He may have been naive when he used to think that the stresses of parenthood would get easier as the kids got older.

* * *

"Jess Mariano," Jess heard his name as he passed Mr Fritz in the hallway between periods later that day, "I don't seem to recall seeing you in this morning's class, I'm glad to see you decided to show up for everyone else's lessons."

"Had a dentist appointment," Jess stated boredly.

"That's funny, your sister said doctors," he raised his eyebrow, catching the student in his lie.

"Well a dentist is a type of doctor wouldn't you say? Unless you're now diminishing other people's professions Sir, but I know you wouldn't do that," Jess spoke with confidence.

"Well I'm glad I caught you, I was hoping to speak with you after your final class. I've noticed you've been slipping a bit on your latest tests and I like to discuss any issues with my students before things get too bad."

"I love the concern, but that won't be necessary, everything's A-ok here Teach!" he assured with faux enthusiasm.

"Jess I know how bright you are, I'd really like to understand what is going on with you lately," the man pressed, "if it continues to happen and I don't know why then I'm going to have to contact your parents."

"Look, I'm fine. I was just busy last week and I didn't have as much time to study," Jess replied. Okay maybe 'didn't have time' and 'didn't feel like it' weren't exactly the same thing, but Jess didn't feel bad for the small lie if it got his teacher off his back.

The man nodded, concern still evident in his eyes, "Alright, well if you are struggling like that again then come talk to me, I'd rather we work something out than watch your grades drop."

Jess gave as respectful of a nod as he could muster before finally pushing past the man and towards his next class.

Math with Ms Harper. Mr Fritz may have been off his rocker half the time, but at least he was an okay guy. Ms Harper, on the other hand, seemed to hate Jess with a burning passion and Jess had to mentally prepare himself every time he entered her classroom.

Now if you asked Rory, she would say that Jess was exaggerating when it came to the woman's hatred for him, and maybe Jess could admit that he may have brought some of it on himself. Math was by far his least favourite subject, however, mostly because he didn't feel the need to be there. The problems were easy and he always felt sitting in the class was a waste of forty-five precious minutes of his day. If he hadn't already skipped out on social studies he would have given himself a day off from math as well.

These facts in themselves always seemed to put Jess in a bad mood and it wasn't five minutes into the class before the teacher already caught the bad end of it.

"Jess do you have your homework to turn in?"

"Nope," he replied with a bit too much attitude and he could see Rory shaking her head from a few seats over.

"And why not?" the lady pressed, their conversation almost routine by now.

"I didn't feel like it was an appropriate use of my time," the teen responded honestly and he could almost hear his sister's sigh.

"Well I hope you enjoyed the free time because you will be spending the afternoon with me in detention," she sentenced.

"Gee still no boyfriend huh? I promise you there's better company than me out there if you used the time you spent with me in detention to actually go out and look."

The comment didn't bode well with the older lady, but even so, Jess didn't manage to get kicked out of class that day, probably a good thing, yet Jess couldn't help but feel slightly disappointed anyway. He was glad the day was almost over.

* * *

"Uncle Luke I need you to sign this," Jess spoke, eyes downcast, as he handed the man the pink paper.

Luke fixed his nephew with a stern look when he realized what it was, "Jess what is going on with you!? This is your third detention slip this week!"

"It's all the teacher's fault, right Jess," Rory chimed in with a smirk, having heard the excuse a million and one times before.

Jess glared at his surrogate sister, but Lorelai muted her daughter before he could speak, "Rory, stay out of what's not your business, please."

Luke held his hands up expectantly when Jess used the interruption as an excuse not to answer his uncle, "The teacher's a b-" Luke gave the boy a warning look and Jess stopped himself, "belligerent snob," he finished, making a face as to say that's what he was going to say all along.

Luke gave him a 'nice try' look before shaking his head, "Jess I really don't care whether you like this lady or not, the fact is, I'm signing these notes every second day lately and I'm done letting it slide."

"I don't need to sit in that class!" Jess protested, "I already know everything she's teaching and then she gets mad at me for not paying attention."

"And when she gets mad, you respectfully apologize and start focusing right?" Luke raised his eyebrow.

Rory snickered from across the room and Jess shot her daggers, "She deserves to be taken down a few pegs," he defended to his uncle.

Luke pinched the bridge of his nose, "She is your teacher Jess, you need to respect her and you need to start paying attention in class," he pointed his finger at his nephew.

"Fine, okay, I will, are we done here?" the teen asked with a little too much attitude for Luke's liking.

"No we're not done here," Luke shook his head in exasperation, "If this is the same attitude you are giving your teachers than I don't think you are planning on working that hard to fix the problem."

Jess sighed, eyes fixed boredly on his uncle, "I already told you I would."

Luke exhaled heavily, realizing that the conversation wasn't going to get them anywhere. Instead, he pointed his finger at the teen's chest, "I mean it Jess, if I see one more of these you'll be grounded until I see an improvement for myself, understood?"

Jess nodded wordlessly. Luke quickly signed the slip and handed it back to the boy, "Go get started on your homework until supper."

Grateful for the excuse to leave, Jess didn't feel the need to mention that it was Friday and he didn't actually plan on doing any homework until Sunday night. Instead, he exited the kitchen and a second later his bedroom door clicked shut. Rory had already retreated to her own room earlier, the small battles between uncle and nephew had lost their novelty long ago. Now the parents were left alone in the kitchen.

"And you thought you missed the terrible twos," Lorelai joked in an attempt to relax her husband.

"He's going to miss his sixteenth birthday if he doesn't smarten up pretty soon," Luke vented still frustrated.

"C'mon babe, it's just a few detentions, I'm sure you weren't an angel in high school either, I know I wasn't."

"I just thought that we would grow out of these school battles eventually," Luke sighed tiredly, "It's like I've been having these same conversations with him since he was eleven-years-old."

"Not everyone's Rory Gilmore obsessed with school Hun, he's managing alright I think."

"I know. I guess I just find it hard to understand because he actually has the smarts to do well in school and he just doesn't want to put in the effort."

"We'll just have to keep pushing him," Lorelai reasoned, "We'll get him there," she assured, patting her husband on the back, "Now I don't know about you, but I'm starving and for once we're all here on a Friday night, when was the last time that happened?"

"You think we should force the kids to go out for supper with us?" Luke smirked to his wife, aware of just how uncool it was to be seen with your parents at that age.

"Nah, we're not that cruel, let's order in," Lorelai smiled as she grabbed for the take-out menu on the fridge and proceeded to dial the number.

* * *

 **A/N- I told you it wouldn't be long before I posted the sequel!**

 **Also just fyi I'm not going to promise weekly updates with this story. It just got too stressful with the first one so I'm just going to say I'll post when I can and I'll try my best to be fast about it! That way I can enjoy writing it a bit more and hopefully you guys will get more quality chapters!**

 **Please review! They help me so much!**


	2. Chapter 2

March 20th 1999

Lorelai sat at the kitchen table as she watched her husband get ready for work. It was still early, especially for a Saturday morning and both teens were still hours from waking up. Lorelai, however, had grown accustomed over the last year or so to waking up to see Luke off to work at least once a week. Not that it was easy for the sleep lover to wake up so early on a Saturday morning when it wasn't absolutely necessary, but it was worth it to have those few minutes of alone time with her spouse. Once she saw him off she would always crawl back into bed for a few more hours, even if the sheets felt somewhat less inviting without her husband's protective arm wrapped around her.

"You know I love that you have your own business, and I'm not going to lie the cooking thing is a huge turn-on, but I still hate that you have to work on Saturday," Lorelai voiced.

"I know, I promise I'll be home by noon though," Luke reminded as he grabbed his keys on the desk.

Lorelai smiled, "I do, however, love that you're taking this so seriously and actually making an attempt to give up some of your control at work. I know it's not easy for you."

"I promised that I would," Luke shrugged like it was no big deal.

"I know," she nodded back, "I just want you to know that I appreciate it... and you," she smiled lovingly as she went in for a kiss.

Luke accepted the gesture before pulling apart once more, "See you at noon?"

"I'll be sitting her all by my lonesome until then," Lorelai drawled dramatically.

"What are the kids doing today?"

She shrugged, "I'm not sure, but I'm gonna bet it's not hanging out with little ol' Mom."

"Make sure they clean up the disaster that was Friday movie night before they go anywhere, I can barely move in here," he complained as he shuffled passed the living room and towards the door.

Lorelai nodded as she hugged the side of the door and watched him move towards his truck.

"Be home soon," he called as he pulled out and Lorelai sighed tiredly, heading back to bed.

* * *

She awoke again at around nine, basking in the silence until around ten-thirty when the teens had shuffled out of their respective rooms in search of cereal.

"Jess did you eat all the Cocoa Puffs again?" Rory complained as she shook the last of the crumbs from the box.

"I'm pretty sure we've already established that it was you who ate them all last time," Jess rebuked, "Besides you know I don't eat those unless we're out of Frosted Flakes and that rarely happens."

"Yeah because Frosted Flakes are so gross nobody but you eats them! It's like eating soggy pieces of sugary paper," Rory scrunched up her nose.

"Alright we're not getting into the great cereal debate again," Lorelai interjected, "What are you two up to today?"

Rory settled for Captain Crunch, pouring herself a bowl as she answered her mom.

"Lane needs help with her history paper and then we're going to watch Jess and Pete play basketball for a bit. I'm supposed to write some sort of sports article for English and I think it would probably be beneficial to at least watch a few minutes of some type of sport."

"Definitely couldn't hurt," Lorelai agreed as she pulled out a chair to sit with the kids, "Just do me a favour Hun and don't try to attempt any of the sport move thingies again, we all know how that went with baseball."

"Luke only had a limp for a week," Jess smirked as Rory stuck her tongue out at him.

"Ok so I don't have the best hand/eye coordination, at least I admit it," Rory rolled her eyes at the banter, "I wasn't planning on moving from my spot on the bench this time anyhow."

"Jess, see to it that she doesn't," Lorelai added playfully, and her step-son nodded seriously, accepting the duty, "So that's all you've got planned for the day?"

"Well, actually, Rory wanted to know if we could go to Pete's tonight for a bonfire," Jess spoke up swiftly.

"Hey, you're the one who wants to go so bad!" Rory countered.

"Are his parents home?" Was Lorelai's first question.

"Yes and don't worry Lorelai we'll even stay a full meter away from the fire at all times," Jess promised brashly.

"Hey don't get sassy with me boy, especially when you're asking for something! Have I taught you nothing!?" Lorelai chastised lightly, "It's fine with me, but I'm going to run it by Luke too. Drop by the diner around lunch and I'll let you know then, and keep those eyes front and center mister! I swear we're going to have to get a doctor's opinion if they keep rolling around like that!"

"Thanks Mom, we'll be there for lunch," Rory spoke up before her brother ruined it all together.

"Oh and make sure you pick up the living room before you go, I think Luke is going to have an aneurysm if he steps in another plate full of marshmallow and syrup," she reminded getting up.

She made herself another cup of coffee as she listened to the kids getting to work in the other room. She sipped slowly, wondering what she was going to do with her day until Luke finished work.

* * *

Just before noon, Lorelai wandered through the town and into the diner. After having a relaxing hour to herself, she had decided to meet her husband at the diner and have some lunch before he would be hers for the afternoon.

"Hey Babe," she greeted, leaning over the counter for a kiss.

"Hey, want some lunch?"

"Cheeseburger and chili fries if you would be so kind," she smiled batting her eyelashes.

"Good morning?" Luke questioned when he came back from putting her order in.

"Quiet. Kids went out for the day, I was able to catch up on my morning soaps. Which reminds me, by the way, Rory and Jess want to go to a bonfire at Peter's tonight, they said the parents are home. I said it was okay, but that I needed to ask you first."

"Ah so I am the bad guy if I say no then, right?" Luke smirked.

"No, just showing that we are both on the same page. What if they had already asked you and you said no and I wasn't aware?"

"Well they never asked and it's fine by me as long as they're home by ten."

Lorelai nodded, "I told them they had to come by the diner for lunch anyway, you can tell them that yourself. I guess that means we have the house to ourselves tonight."

"We're not watching a Lifetime movie!"

"Oh come ON Luke! You know the kids always complain when I do!"

"I can't believe we have the house to ourselves and you want to watch a movie."

"Well we could give baby making a try, but we've both agreed we don't want any more kids right now."

It was true the discussion had come up more than once in the couple's short marriage. At first they both had thought that maybe a baby, one that was a perfect mixture of both Luke and Lorelai might be nice. However, with the blending of their families together, the home renovations, both parent's full-time jobs and rapidly growing kids, the couple had agreed that the longing for a newborn wasn't as strong anymore. It hadn't been ruled out completely, they were still relatively young parent's after all, but as of now the pair was perfectly content with their family of four.

Luke gave his wife a somewhat annoyed, yet equally bemused look and the woman caved, "Alright, I think I can scrounge up the party favour from my eighth grade health class and give you a little somethin' somethin'."

"Lorelai!" She watched as the man's face grew red and eyes darted around the room.

"Chill Babe, nobody's listening," she laughed at his expense.

"This is Stars Hollow, everybody's listening," Luke countered.

However, before she could reply she was interrupted by the sound of their dependents entering the building, their mostly playful bickering announcing their presence far before the bell above the door had done its duty.

"Rory stole our basketball and ended up smacking herself in the face," Jess tattletaled like they were five-years-old, his snickers earning him a smack to the arm from his sister.

"I did not steal the ball! It rolled over to me. No comment on the smacking myself in the face part," her face blushed pink, aiding to blend in the slight discolour from where the ball no doubt had hit her.

"I thought we agreed you were to go nowhere near the ball Missy! Jess you were supposed to be watching her!" Lorelai reminded in faux disappointment.

Jess raised his hands up in defence, "Hey I was running after it! It's not my fault she picked it up and decided to try bouncing it back to me!"

"Basketballs are unpredictable! They never go the way they are supposed to," Rory defended meekly.

"I'll get you some ice Rory," Luke smiled sympathetically if not somewhat amused by the conversations he seemed to find himself watching on a daily basis.

"Thanks Luke."

"So other than the minor bruising did you get everything you needed to write your paper?" Lorelai asked.

"I think so, though this might be the first time Jess can actually help me with my homework instead of the other way around," she joked.

"I never need your help," Jess retorted.

"No you just want me to do it for you," the girl countered.

"Alright, I think this is the point of the conversation that Mommy is supposed to tune out," Lorelai spoke up. She knew that Jess' enthusiasm over school was less than satisfactory and though the couple tried their hardest to get Jess more engaged in his work, she also trusted her daughter to help her brother out whenever she could. She would, however, like to keep the mindset of that involving tutoring, and not cheating. She knew Rory though. She was a good kid, and above all took her work seriously. Lorelai knew if there was a bit more help from Rory's department than she would care to admit, she also knew that Rory wouldn't allow it to get too out of hand. They all were well aware that Jess was more than capable of doing the work himself after all.

Luke finally returned, passing the bagged ice over to Rory who pressed it gingerly to her face, wincing slightly from the harsh coolness that bit beneath. Luke turned around once more, grabbing three plates of food, guessing what the kids might want as well as fulfilling Lorelai's request. Neither teen spoke about their lack of option as they dug into the plates placed in front of them eagerly. Luke would swear they were both in a growth spurt again with how much food they seemed to be indulging in lately. He noticed, especially Jess, had seemed to be hitting growth spurts every few months now, and it was definitely showing in the way that the boy's ankles were on display in nearly all his pants now. Another trip to the mall would need to be scheduled again, the uncle mused. He had been hoping they could have at least lasted the spring since the new clothes would only be needed for another few weeks before they would be into summer clothes and the boy would no doubt need a whole new set of warmer clothes again by fall.

"So," said boy spoke up, mouth full of chili fries, "Tonight?" he questioned eagerly.

"Yes you may go," Lorelai obliged.

"You will be home by ten though," Luke added.

"It's Saturday!" Jess predictably argued.

"Yeah and you're fourteen," Luke reminded.

"Fifteen," Jess countered seemingly offended by being demoted from his newly established title of fifteen-year-old.

"Whatever, Rory's still fourteen and you're barely fifteen. You do not need to be out until all hours of the night. Now it can be ten or not at all, your choice."

Jess huffed, but Rory spoke up first, "Well I don't know about Jess, but I choose ten. It will be too cold to be out too late anyway Jess," she encouraged the boy to see reason.

"Fine," Jess agreed and Luke was grateful he didn't try for round two.

Luke wasn't too worried. If his nephew had been going alone he would have been more prone to wondering if Jess had only agreed to the ten o'clock curfew to get the man off his back, deciding to himself that he would stay out until whenever he wished and accepting the grounding when he got home. However, Luke knew that with Rory accompanying the boy, the two were much more likely to get home in one piece at the designated hour. Rory just seemed to have a way with Jess that neither of the parents could quite reach.

"Good choice," Lorelai praised, clapping the boy on the back, "Now will you guys be home for supper first?"

"No Pete said we were going to roast hotdogs on the fire if that's okay?" Rory asked.

"Sounds fun," the mom smiled, "Well it looks like a dinner date and a nice Lifetime movie are in the cards for us Lukey!"

Her three family members groaned loudly, and Lorelai happily set off to defend her beloved source of entertainment.

* * *

March 21st

Jess was lying on the couch as his open book rested neatly on his stomach, held up by one hand while the other arm draped tiredly over his forehead. His eyes were fixed in concentration, not even noticing his uncle coming down the stairs until he was standing over him. Jess threw his eyes back, looking upside down at his uncle expectantly.

"Yes?"

"Good morning to you too," Luke greeted, "I didn't expect you to be up this early after last night."

"And again you're under the false pretense that ten is an outrageously late time to be out," the boy lipped sarcastically, "I could also counter that I wouldn't have expected _you_ up so early after last night," he added, fixing the man with a scandalous look.

"Please stop making assumptions about mine and Lorelai's alone time. You know your last loud remark caused me a week of annoyances from this nosey town, and it wasn't true might I add."

"Hey, I don't know what you two get up to up there, all I can go by is what I see with my own two eyes."

"You watched that stupid bird at the fair bite me with your own two eyes Jess! Telling the town it was a love bite from Lorelai was just being a nuisance!"

Jess bite back his laughter, following his uncle into the kitchen, "Are you making breakfast? I'm starving!"

"You're always starving," Luke pointed out, "And I should let you starve for all the trouble you cause me," he threatened, already reaching for the fry pan in the drawer.

"You'd never do that to me. Besides, I'm ten times more annoying when I'm hungry," Jess warned.

"Do you want eggs or pancakes as your last meal?" the uncle spoke dryly.

Jess pretended to ponder the question for a moment before answering his uncle, "Well I suppose if this is my last meal, then I should have both, shouldn't I? I'll want it to last me a while and though pancakes are quite filling they never really last too long. The protein in the eggs will keep me going for hours, though."

"You're going to eat me out of house and home one day, you know that?"

"Oh and your wife isn't?" Jess laughed.

Luke couldn't argue there, "Alright enough out of you, come help me with the eggs. If you ever want to be able to do more than bus tables at the diner you're going to have to learn how to cook."

"You mean someday you're actually going to treat me like a big boy and let me cook?" Jess asked in awe.

"Maybe when you're actually old enough to be allowed there by law," Luke countered, "Now get some eggs to crack."

It wasn't the first time the boys had cooked together. Luke had fond memories of helping his mom out in the kitchen when he had been small and he was grateful for those memories, as well as the skills it taught him to be able to cook for himself. He wanted his nephew to develop those same skills so that he could cook for himself when he was grown up and out on his own. That was what he would tell his nephew anyway, and it was true, but secretly Luke could also admit that the time spent with the boy, especially as fast as he was growing, was nice. Cooking also seemed to be a task that both boys shared a liking to, which was a bonus when trying to bond with a teenager.

"So," Luke spoke casually, "How have you been doing lately? Anything new?"

Jess shrugged, and Luke expected it. Still, he always liked to try to catch up with his nephew when it was just the two of them. He knew that the boy was going through some things right now. Luke guessed it was most likely just growing up and being a teenager, but he still worried for the boy. It was easier when he was younger, when he could (usually) convince him to talk. These days the boy was quieter and though he was more than comfortable living with the girls, the uncle still found it hard to get his nephew talking about his problems while they were around.

"Same old same old," was Jess' vague response as he concentrated on cracking an egg over the fry pan, causing a satisfying sizzle.

"There's got to be something interesting you've got to share," Luke pressed, "How're the guys? Pete good? He ever tell that girl he liked her yet?"

"Kim? Nah, he's been over her for weeks," Jess informed.

"What? He was head over heels for that girl!"

"Yeah, but that was before Briana transferred to our school. You'd understand if you saw Briana," the boy added when he saw his uncle's flabbergasted expression.

Luke let the conversation drop after that, not willing to get into the dramatics that was Stars Hollow High School. He had been out of there a lot of years now and sometimes the stories his nephew brought home from that place made him wonder how he ever made it through those years. Jess himself seemed to mostly stay out of the drama. He had yet to get a girlfriend of his own, even though Luke had noticed his increasing interest in girls as early as his thirteenth birthday. But still, his nephew had his small circle of friends and was perfectly content with watching the hysteria from the sidelines, most of the time at least. Luke was glad that the boy was doing a much better job these days about staying out of fights with the other students, now if only he could keep his mouth kinder towards the teachers.

"So, I was thinking..." Jess started once more after the boys worked a few minutes in mostly silence.

"Oh no," Luke responded. Usually when Jess 'thought' it was either really good or really bad.

"It's not bad. I was actually hoping we could spend the day together, now how terrible is that?" Jess asked in mock hurt.

"And the catch would be," Luke pressed on.

"No catch," Jess shrugged, watching his uncle give him a look. "Fine," he sighed, "I have birthday money left and I was hoping you could drive me to Hartford to that really awesome bookstore so that I could spend it."

"So you need a chauffeur."

"C'mon Uncle Luke, don't make me beg. In another year I can drive myself and I'll be out of your hair."

"Oh yeah that really makes me feel better," responded Luke, not wishing to think about his nephew loose on the streets with wheels.

Jess fixed his uncle with his best pleading eyes, the same look he had been using on his uncle since he was eleven and Luke caved, "Fine."

Jess smiled wide before nodding his head casually and tending to his food once more.

"Now were you hoping to have just a you and me day or do you want to invite the girls as well? It's up to you."

"No, they can come if they want to," Jess answered honestly, "I know Rory loves that bookstore as much as me."

Luke nodded, glad that his nephew never seemed to have an issue with sharing his uncle. It probably helped that at least one day a month the boys took a day to themselves while the girls did the same. It was great that the family all got along so well, but those bonding days proved to be incredibly important as well.

"Ok great, maybe we can go see a movie or something while we're there."

"Rory's probably going to want to drive by Chilton too," Jess smirked, knowing full well how much the girl wanted to be accepted at the school.

"Well we might as well make an outing of it if we're going. Why don't you go wake Rory and I'll finish breakfast."

Jess nodded, passing the spatula over to the man and disappearing through the girl's doorway. Luke smiled as he finished up the breakfast. He and Jess had made many trips to Hartford over the years, yet their first venture still stood out to Luke as the best. He could still remember Jess' silent pout when the uncle had beat him over and over at go-karting, as well as the triumphant grin when he had finally crossed the finish line first. That was the same trip that the uncle had introduced Jess to the special bookstore for the first time and Luke would swear he had never seen a kid's eyes bulge out as much as that. Jess was right, it wouldn't be long before the teens had their driver's licenses and they would be hanging out with their parents even less than now. It seemed they had transformed into teenagers overnight and every day he noticed them getting more independent. He could feel the clock ticking and he decided that he was going to enjoy these days while he could.

* * *

 **A/N- The filleriest of filler chapters, but I wanted to establish a bit more of the family life before diving into the plot. The next chapter will be more interesting I promise! I have a lot more of this story planned then I did the last one and I think that actually makes it harder to write these types of chapters because I just want to get to my plans already! Please review if you have a moment and thank you so much to everyone who favourited, followed and reviewed chapter 1!**


	3. Chapter 3

April 1st

"Jess... Jess. JESS."

Jess was snapped out of his daydream, turning from the window where the sun shone a perfect spring day. Too perfect to be cooped up in a classroom that was for sure. Rory had been keeping a better eye on her brother lately, however, and she was making it much harder for him to skip classes. He had just been thinking that perhaps he could cut out after English. The siblings didn't have science together, the only class they didn't share, and it was the perfect time to skip out without his sister's judgemental eyes on him. He was only allowing himself one skipped period a week now. Luke had been starting to get irritated from the constant detention slips and though he didn't know about the missed classes, Jess knew his luck would run out eventually. He needed to be more careful. His breaks wouldn't be worth much if it meant that his free time would be taken up by being grounded to the house.

"Jess Mariano," his history teacher called once more from the front of the class. It was only then that he noticed all eyes were on him, "Are we boring you, Jess?"

Yes was the short answer. Jess had zoned out as they were discussing World War I and though that in itself wasn't exactly considered boring, Jess had already read more books than he could count on the subject and he was sure come test time he would ace it no problem. His history teacher was an okay guy, however, and Jess didn't feel the need to be hostile towards him.

"I was listening," he lied.

"Were you?" the man raised his eyebrows in doubt, "There will be a test on the subject on Tuesday and you need to know this."

"I was listening," Jess repeated.

"Ok Jess, what year did the war start?"

Jess expected the questioning and replied easily, his decision to curb the hostility now out the window. "Well the answer's right on the blackboard, 1914, but if you want to be more specific it was July 28th. However, many would argue that it initially started on _June_ 28th when a Serbian terrorist assassinated the Austria/Hungarian Archduke. It ended November 11th, 1918 by the way, oh sorry it looks like you haven't gotten to that part yet, didn't mean to spoil the big finale."

The teacher sighed as Jess looked expectantly to the man, "Thank you, Jess, that will be quite enough. I'm glad you seem to already know the material, but I would still appreciate it if you paid attention."

Jess smirked to himself as everyone turned back to the front of the room and the teacher continued his lesson. He loved to watch the teacher's face go from pompous to annoyed in two seconds flat when they tried to stump him with a question, only for Jess to prove them wrong. He looked over at Rory who was still looking at him, shaking her head slightly, yet Jess could tell she had been equally amused by the entire scene.

Once the bell rang, Jess exited quickly, glad to finally be free from the room. Rory caught up to him, her books hastily stacked in her hands, "You're unbelievable, you know that?" she smirked.

"Hey, they should really learn not to doubt my abilities by now."

"Never doubt the great Jess Mariano," Rory joked with an impressed smile, "You know, you're really lucky you have all that information stored up in that big head of yours, I noticed you zoned out a good thirty minutes before he called on you."

"What can I say," Jess shrugged cockily.

"I have something to say, it's not fair! I'm going to have to study hours for that test on Tuesday and you're just going to float through like you always do," she rolled her eyes.

"And yet still you prevent me from cutting a few pointless classes."

"Yeah, because if you don't have good attendance they'll hold you back anyway, no matter how good your grades are," She pointed out, "Plus you skipped way too many social studies classes in a row and you almost failed those two tests, remember?"

"So I miscalculated," the boy shrugged, "Besides, he threw in questions that were specific to class discussion. That wasn't fair."

"It was totally fair if you attended those classes," Rory rolled her eyes once more, "Now come on, we have English and I know that's one class you actually like."

English was pretty much the only class Jess did pay attention in, and also the only class he never skipped. Most of the books they read he had already read more than once, yet the class discussions were usually interesting enough, even if the boneheads in his school didn't know good literature if it smacked them in the face. He also enjoyed writing. The essays were no problem for the literati and the teacher, Mrs Truly, was a pretty cool lady who always enjoyed hearing Jess' opinions on various topics. She always asked about the new books Jess and Rory brought into class with them, smiling when the books would be different from one class to the next. When she had first noticed just how much the two seemed to read, she even allowed them, on occasion, to do separate assignments from the rest of the class, wishing to challenge them on books they hadn't read twenty times before. Jess never felt bored in her class and he appreciated that.

English class had relaxed Jess a lot, and when class was over, Jess actually felt pretty content. He considered the possibility of staying for the last period, even if just to continue his reading in the back. Though, when he parted ways with Rory the urge to enjoy the spring day before his shift at the diner won out and Jess found himself heading for the back door instead.

The warm breeze hit his face and Jess breathed in the fresh air. Between English class and this, he could definitely feel his day turning brighter and instantly he was happy that he hadn't dragged himself to the science lab. The fresh air was certainly more enjoyable than the formaldehyde scent that clung to the lab walls.

Jess took the short walk to the bridge with ease. Enjoying the first nice day in a while and longing for the summer months when he could be free of books and classrooms altogether. When he eventually reached the bridge, he sat down and stretched out his legs, letting one foot dangle over the edge, just skimming the water. He cracked open his book and lost himself in the world within the pages.

* * *

The voices didn't register with him immediately. The story was getting to the climax and his ravenous reading had distracted him too intensely. When the sound finally did break through his trance he shot up in a second.

Sookie's giggling is what gave them away first, followed by the distinct sound of Lorelai's hyper chirping. Grabbing his things, Jess dashed to the nearby shrubs and awaited their presence.

"Ugh I'm glad Taylor's decided to raise money to fix this rickety old thing," Lorelai's voice broke through the air as she and Sookie finally came into view, "I know Jess and Rory love to hang out here, but I'll feel a lot better once it doesn't look like it's going to fall apart from under them anymore."

"I know. I tripped on a loose board over there the other day and nearly fell head first into the lake," Sookie divulged. Jess could argue that loose board or not, Sookie would find a way to fall head first into the lake, but his attempts to stay still and quiet pushed those thoughts from his mind.

He was irritated. Lorelai never walked back to town this way. Usually, she took the dirt road that lead straight back to the center of town. His relaxing afternoon of reading was rudely interrupted and now he was one wrong move away from getting caught. His calves were getting sore from the crouched position he was in and as luck would have it the girls had found a frog near the edge of the bridge that caused them to stop and admire.

"Aw look at the little guy bathing in the sun," Lorelai gushed.

"He is pretty adorable," Sookie agreed.

"Hey, I dare you to kiss it," Lorelai smiled widely, suddenly getting excited, "Ooh! Maybe he will turn into your Prince Charming!"

"Ew! I'm not kissing a frog!" Sookie declared, "If that's how I have to find my Prince Charming then I'll stay single forever."

"Aw c'mon," Lorelai nagged, "Just a little kissy-kissy."

Jess' legs were failing him, the strain burning the back of his calves like fire as he watched the scene before him. Without warning they gave out from underneath him, causing him to fall on his butt none too gently and the bushes in front of him rustled with betrayal.

"What was that?" Sookie asked, turning from where they were crouched beside the frog.

"I don't know," Lorelai spoke and Jess' heart raced as he attempted to keep as still as possible lying on his back. From the edge of the bush, he could make out the women moving to get up. Suddenly the giant frog that they had been admiring jumped to life, landing on Lorelai's foot. Both ladies shrieked as Lorelai shook her foot, causing the frog to fly through the air and rest near the front of the bush that protected Jess. The two women dashed away as Lorelai cried about needing to disinfect her foot.

When he could no longer hear their frivolous yells, Jess let out his breath slowly, never realizing how hard he was holding it. He stayed lying in the grass while he waited for his pulse to return to normal before finally getting up. School was just ending, he realized as he looked at his watch. Collecting his things once more Jess headed in the direction of the diner, not wanting to be late for his shift and causing Luke any suspicion. He silently thanked the giant frog as he passed it by and it croaked loudly in response. That was close. Too close.

* * *

Jess made it to the diner just as the school crowd had filtered out of the building across the street. He saw his uncle at a table taking an order and nodded in his direction, heading behind the counter to set down his things and grab a coffee pot. Luke approached him a moment later.

"Hey, how was school?" he asked handing the order to the kitchen.

"Fine," was Jess' go-to answer. He figured by now Luke only asked him that out of habit instead of expecting any sort of in-depth answer.

"Good, well those tables could use refills and then- why do you have leaves in your hair?" the man furrowed his brow as he grabbed the plants from his nephew's head.

He was taken off guard for a second, throwing his hand to his head where indeed there were leaves clinging to his hair. Quickly Jess scrunched up his face in annoyance, "That jerk Presby threw a bag of leaves on my head. Who even does a project on leaves to begin with?"

"Seriously?" Luke answered, shaking his head, "Jeez you at that Presby kid have been at each other's throats since elementary school. What did you do to him?"

"Nothing! I've never done anything to him, he's just a jerk," the boy complained. "Who cares anyway, it's just leaves, right?"

"I guess," Luke nodded, although he didn't like the idea of some kid picking on his nephew.

"Well I better fill up their coffee," Jess reminded, motioning towards the customers.

"Yeah, go on," Luke nodded, stepping out of the teen's way, "Table three needs a wipe down, do that once you're done.

Jess nodded as he got to work. He hoped that would be the last of his close calls for the day.

* * *

After work, Jess and Luke walked home together, dinner in hand since both boys had agreed they were too hungry to wait for Luke to cook something once they got home.

"Dinner's here!" Jess called when they walked through the front door, Luke giving him an annoyed look at his unnecessary volume.

Luke pushed past him towards the kitchen to set the bags down and Jess went in the direction of the living room. As he turned the corner Rory popped her head up from where she was sitting on the couch with a textbook in her hand, "Where were you after school? I was waiting for you!"

"I worked at the diner today, you know that," Jess reminded her.

"You must have left pretty fast because I didn't see you anywhere and my classroom was right next to your locker."

"Mr Carlton released us a few minutes early since we finished our lab," Jess lied, knowing that it was better not to divulge his misdeeds to the girl this time, "I would have waited for you, but you know that Luke hates it when I'm late."

"Fine," Rory sighed, "But I wanted to show you the CD Lane found at the record shop in Woodbridge!"

"You can show me after supper, I'm starving!" Jess promised, ushering the girl into the kitchen where Luke and Lorelai had gotten the plates and utensils out.

As the family sat down to their Chinese feast, the topic turned to stories of their day.

"Lane and I went to the bridge after school to look for rocks for our science project, but there wasn't many there," Rory recalled to her family.

"You should try over by Larson's dock," Luke suggested, "There's that little rock beach over there."

"Oh yeah! I forgot about that place!" Rory smiled, "We'll have to go check it out tomorrow."

"Hey, speaking of that bridge, I don't think you kids should be hanging around there so much anymore, I think there's a bear or something living there!" Lorelai warned seriously.

"A bear?" Luke furrowed his brow, "What makes you think that?"

Lorelai shrugged, "I don't know. There was definitely something rustling in the bushes when Sookie and I walked by earlier."

"I think if it was a bear you would have seen it through the bush Mom," Rory pointed out, "Maybe it was a rabbit or a bird."

Jess tried his best to keep his expression neutral, not feeling like he was in any danger of the truth coming out now.

"Possibly," Lorelai reasoned, "I still think you two should be careful though, that old bridge is falling apart."

"Speaking of the old bridge, Taylor called me today," Luke all but rolled his eyes, "Was asking if I knew anything about the bridge repair donations going missing."

"He will not get over the fact that I stole a few candy bars from him when I was twelve!" Jess shook his head. Every time something happened in the town since then, Taylor always seemed to think it was somehow Jess' doing, "I hope this isn't your way of asking if I took it?"

"Of course not, I know you wouldn't do that. I think your days of stealing are long over," Luke assured.

"That's for sure," Jess agreed, remembering just how much trouble he had gotten into the last time he had attempted a career in theft.

"I hope you told him where he could stick it," Lorelai snarled, shaking her head. She knew their boy was good and she hated that although most of the town now looked out for him and loved him just as they did Rory, others still judged him so harshly for things he had done when he was younger and misguided. Hell, didn't everyone do dumb stuff when they were young, regardless of their upbringing?

"He won't be calling around the diner anytime soon," Luke assured with a nod.

"Good," Lorelai replied firmly, "I'm still sitting on that bit of blackmail I have on him. He knows I saw what his grandson did to the drinking fountain last summer. He better not push my buttons!"

"He wouldn't dream of it," Luke chuckled, grabbing the empty plate from in front of his wife and carrying it to the sink along with his.

As Rory finished off the last of her own plate she looked eagerly to Jess, "Can Jess and I be excused? I still want to show him that CD."

"Go ahead," Luke agreed, "We'll clean up here."

"Thanks!" Rory smiled, grabbing Jess' hand and dragging him into her room.

Jess allowed himself to be pulled without a fuss. The thought of spending the night listening to music with his surrogate sister didn't sound half bad after a long, stressful day. Closing his eyes, he found peace in the lyrics and melodies.

* * *

April 2nd

Luke was busy in the diner the next morning. For some reason late Friday mornings were habitually a busy time for the place and Luke felt like he hadn't stopped since he had stepped through the doors. He was just placing a plate down in front of a customer while noting a request for more peanut butter from one table over when the phone rang and one of his part-timers called him over, informing the man that it was for him. Sighing, Luke set down the coffee pot he held in one hand, gave direction to the younger man to bring peanut butter over to the awaiting customer and took the phone.

"Luke Danes," he greeted as he pressed the phone to his ear.

"Mr. Danes? This is Principal Merton from Stars Hollow High. I'm calling in regard to your nephew Jess Mariano?"

Luke let out a heavy sigh as he pinched the bridge of his nose. He had to admit it had been a while since he had received a call from the school, yet still, he couldn't help but feel annoyed with his nephew anyway.

"What happened?" he finally asked in a tired voice.

"I'm actually calling to set up a meeting with you," the man informed.

"What's going on?" Luke questioned once more, growing concerned.

"I really do feel that this conversation would be best had in person Mr. Danes," the principal pressed, "Would you be able to come over to the school later today?"

Sighing once more Luke nodded, only then realizing that the man on the other end couldn't see him. "Just tell me what time works best and I'll be there."

"Wonderful. Would noon work for you?"

"That should be fine," Luke agreed.

"Wonderful," the principal repeated causing a shot of annoyance to pass through Luke. The guy had managed to use that word twice within the last ten seconds when, in fact, nothing about the situation felt all that 'wonderful.' "So we'll see you at noon."

Before Luke had the chance to respond the principal had hung up, leaving Luke standing in front of the phone with dread. He had no clue what the man wanted to discuss and he sort of wished he had divulged a bit more information about their meeting. There was only about an hour until he was supposed to be there, however, leaving Luke just enough time to worry about just what his nephew had gotten up to now.

* * *

 **A/N-** **Ooh! What do you think he wants to discuss!?**

 **Thank you for the reviews on the last chapter! I'm glad so many of you were happy about the Uncle/Nephew and Mother/Daughter days! And to those concerned, yes they do have special days with the opposite kid as well! None of those days are a scheduled thing, but they do try and do it as much as possible! (I actually thought I put that in the chapter, but I suppose it was just floating around in my brain and never made it haha)**

 **Also, to the person who reviewed about Jess' age and grade, I did think long and hard about that when I was first deciding his birthday. The US school system always confuses me because in Canada we start school at four and if your birthday is past September you can start at 3 or wait a year until your four. However, it seems the US has a whole bunch of different rules. Either way it confused me a great deal! When deciding Jess' birthday I tried to look up when it might have been in the show, but I couldn't find anything! After I had written in his birthday of course this big post comes up with a bunch of theories of when his birthday was and now I wish I would have made it in August/September because it would have made more sense. Especially because we know in the show Rory and Jess were in the same grade. I can't go back now, however! So we're just going to have to ignore it and in my mind Liz was just negligent and didn't even realize Jess needed to be in school until a year later! :)**

 **As always reviews are appreciated.**


	4. Chapter 4

April 2nd

At twenty minutes to noon Luke couldn't take it anymore and although he was literally a few steps from the school, he had hollered to Caesar and announced that he was leaving and would be back soon. Now that he was standing in the school entrance, however, seventeen minutes remaining until their meeting, he realized that he couldn't really head straight for the principal's office, and suddenly he felt foolish for arriving so early.

Walking down the hall brought back memories that Luke would have preferred to keep buried. He had always felt uncomfortable when the kids were younger and he needed to go back to his old elementary school, but now that Jess and Rory were in high school, and the need for his visits had decreased considerably, he had less experience revisiting the old building where he spent (or tried to avoid spending) his teen years. He laughed to himself remembering how often he would skip classes when he was younger, to the dismay of his dad, instead opting to help out at the hardware store. Yet, the man, just having lost his wife, never said much, as he needed the help and the family needed money. Luke shook his head, realizing not for the first time how much he and his nephew were alike. He could admit that school hadn't been his thing either, but he also knew that Jess was a lot brighter than he was, whether he wanted to apply those brains or not was up to him.

The halls still smelled the same as they had all those years before. A mix of teen odour and excessive Axe spray making Luke's nostrils clench from the intensity. To-go coffee mugs, many from the diner, piled on top of the over flowing garbage and Luke shook his head wondering at what age the caffeine addiction became considered normal. He was aware that over the past few years Rory had grown increasingly interested in the beverage that her mother worshipped, and to Luke's dismay, Lorelai had no issues with allowing her still young daughter to indulge in the bad habit as well. It had caused quite the fight between the couple when the issue was first brought up. Lorelai had offered Rory a cup one day, which had caused Jess to become interested as well. It was the first time that the parents' rules had conflicted and although he wouldn't have let Jess drink coffee at thirteen under normal circumstances, he had no choice but to pick his battles. The two kids lived in the same house and the same rules needed to apply for both of them. Luckily for him, Jess hadn't taken much of a liking to the hot beverage anyway.

Passing the mess of lockers, many of which not even bothered to be locked, he casually peeked into a classroom window as he passed it by, a few heads turning lazily to the door when they noticed the movement outside. He chuckled to himself at the post-lunch crash that seemed to have hit ninety percent of the students in the room and Luke felt for the poor teacher who was trying his hardest to produce some sort of reaction out of his tired pupils.

Stopping right before the trophy case where he and Lorelai had found incriminating high school pictures of him when they had visited on parent's night, Luke checked his watch and noticed he had killed nearly fifteen minutes. He decided it was now appropriate to make his way to the office and he tried his hardest not to jog there in anticipation.

He arrived in the waiting room and was greeted by the receptionist who checked him in and told him to wait in one of the plastic chairs lining the walls. He felt transported back to his younger days as he sat outside the principal's office and he squirmed out of habit. It was only another minute or so before the door swung open and the man who Luke had met just once before walked out.

"Mr. Danes? Hello, it's nice to see you again," he greeted extending his hand.

"Uh, yes, you too," Luke replied, wiping his hands on his pants as he got up to accept the hand.

"Why don't you follow me into my office and we'll talk."

Luke did as told and was surprised to find two other individuals in the small office when he entered.

"Mr. Danes, this is Mr. Blakes, Jess' History teacher, and Mrs. Truly, his English teacher. They'll be sitting in on our meeting as well."

Nodding politely, Luke inadvertently gulped, wondering just what his nephew had gotten himself into if it meant the principal needed back up to confront him about it, "Hi," he replied, shaking their hands respectfully before taking a seat in the empty chair.

"Now I know you're probably wondering why I asked for this meeting with you. I honestly didn't mean to be mysterious," the man chuckled from behind the desk, "I just thought it would be much easier to discuss this in person."

Luke silently nodded, reminding him more of Jess than himself.

"I'll let Mrs. Truly have the floor to explain the situation," the man gestured to the younger woman and she smiled warmly.

"Mr. Danes, your nephew is an exceptional student," she began, "I've never quite met a young man who reads as much as him and he has such a way with words in his writing it trumps even my skills. You should be very proud."

He waited for the 'but' to come. He had heard the speech before, 'Jess is very bright, but he doesn't apply himself,' he knew the line and he sighed internally waiting for it to fall from her lips.

"I noticed right away that he was special," she continued, "And over the past few months I've been noticing that the materials we were studying in class just weren't challenging enough for him. I've recently started giving him separate assignments from the class and he has seemed a lot happier with the new material."

Luke nodded to let her know he was paying attention, though, honestly, he was no longer sure where the conversation was going.

"I started asking around to Jess' other teachers, but to my surprise they all had very different reports of my star student. Mr. Blakes has filled me in on the Jess he sees in his class and I have to admit I was a bit perplexed."

Mr. Blakes nodded, "I agree that Jess is exceptionally bright, but in my class and with my other colleagues, he just doesn't seem to be applying the same initiative. I would go as far as saying he is simply bored. I've caught him daydreaming countless times in my class, that is when he shows up, as the amount of classes he skips have been building up considerably. Yet, if I were to ask him a question on the material he can answer with more knowledge than I have taught."

"So what exactly are we getting at here?" Luke finally spoke up, "I know my nephew doesn't show a lot of enthusiasm towards school. I didn't know about the skipping classes, but I can talk to him about that. Honestly, this is a problem I've been dealing with since elementary school and I appreciate the concern, but-"

"Mr. Danes, I don't mean to cut you off, but maybe I should get to the point," the English teacher smiled, "The ninth graders all took standardized testing a few weeks back, and the school received the results the other day," She explained. "Jess' scores were exceptionally high. Number one in the school actually."

Luke blinked, "Wait... what?"

"It's pretty remarkable Mr. Danes," the principal spoke up, "The school hasn't seen a score like that in a very long time. Your nephew is, well... gifted."

"I mean, we always knew he was smart..." Luke trailed, "What exactly does this mean for him?"

"I know we had you and your wife in here not long ago discussing options for your step-daughter in regard to Chilton," he answered and Luke nodded slowly, "Well, we think that it might be the right choice for your nephew as well."

"Chilton? Jess?" Luke asked. The two words together almost sounded funny to him.

"I can understand your reservation Mr. Danes, but we feel that if Jess was challenged more like Mrs. Truly has been experimenting with in her class, his attitude toward school may improve as well," the man explained.

"When you have a child as bright as Jess is," Mrs. Truly picked up, "Sometimes they become so bored with the easy material that they act out. They don't feel the material is worth their time so they simply refuse to do it. They are bored in class so they become a distraction to the other students, or they just don't bother showing up at all."

"It's obvious that he is by far the smartest in his grade," the principal informed, "Yet with the amount of missed classes and unfinished homework I'm afraid he will be on the verge of failing if he doesn't improve."

"I didn't know it had gotten that bad," Luke rubbed the back of his neck, "I know Rory keeps an eye on him and I just figured she'd say something..."

"Sometimes it's not so easy ratting out your brother," Principal Merton pointed out, "Look, I'm sure he figures a class here and a missed assignment there is no big deal, but the fact is his grades have been slipping since the new semester."

"We really do feel that Chilton will be a step in the right direction for Jess," Mrs. Truly smiled, "Like I said, he is doing very well in my class and Chilton has the advanced material that we think he is in need of."

"It really is up to Jess Mr. Danes, but we sent in his test scores to the school and they said they have a place for him in the fall if he wants it," the principal added.

Luke raised his eyebrows in surprise, "He's in? Just like that? We haven't even heard back about Rory yet."

"With her grades and diligence I have no doubt in my mind that she will be accepted too," the man promised, "The truth is the school hasn't started accepting anyone for the fall semester yet. However, with Jess' impressive test scores, they've pushed him through as an exception."

"That's... I mean if this could help Jess," Luke stuttered, still in awe.

"We don't need an answer today," Principal Merton assured, "Go home and discuss it with Jess, see what he thinks. It is a big decision."

Luke nodded in a bit of a haze as he stood up from the chair, "Thanks, I will."

The principal smiled, "Call me back when you make a decision and we will get all the logistics figured out at that point. For now, I'm going to speak with his teachers about coming up with some advanced work for him for the last few months."

"That would be great," Luke agreed, "Thanks a lot."

He turned to head out, but the younger woman rested a gentle hand on his arm as she too made her way towards the exit. "He really is a special kid. You should be insanely proud of him."

The uncle blinked once before letting a smile small spread on his face, "I am."

* * *

Luke left the meeting with his mind still swimming with thoughts. The discussion had definitely taken a different direction to what he had been expecting and he felt a sense of relief and fear all at the same time.

For the most part, Jess was alright. He would need to work with him to get him through the last two months of school, put his foot down about the skipping and homework, but the prospect of Chilton gave the man a solution he had never considered before. After all the years of fighting with the boy, worrying about his future, there were suddenly answers. Positive answers and a plan for improvement. His boy, his _gifted_ boy, might be alright after all.

He smiled to himself as he turned the corner towards the back of the school. He knew Lorelai was still on her lunch break and he decided to head home to catch her before she went back to the Inn. The truth was, he needed to talk everything out with someone before all the rambling thoughts drove him insane.

He walked towards the back of the building and turned when he heard laughing coming from the far corner. A group of boys crowded around the old school dumpster and Luke shook his head at the delinquents. As he passed them by he shot a disapproving glare their way, feeling like he was getting closer and closer to becoming the grumpy old man of the town. However, as he passed by, the corner of his eye caught something familiar, a bit too familiar, causing him to stopped dead, praying that he was seeing things. Unfortunately, zeroing in on the teens only confirmed his concerns. There in the middle of the crowd was his nephew, lit cigarette dangling from his mouth and easy smirk on his face.

Luke's heart sunk as he watched his nephew take a puff of the cancer stick, feeling anger and fear fill up inside him all at once. Before he could even think, he found his voice taking over.

"Jess William," Luke bellowed from across the street and the uncle watched as his nephew's eyes shot towards him when he heard the familiar voice. Quickly, he dropped the glowing stick, smoke rising from the foot that refused to stomp out the heat.

He watched as his nephew cheeks instantly burned red in embarrassment. Luke was unsure if it was because of his uncle's loud exclamation of his full name, or the fact that the man had caught him in the act and he was ashamed. Either way, by the look of the man's face and the firmness of his voice, Luke was sure that the boy's friends were fully aware that he was in deep trouble and Luke bet that it was hurting his pride a fair amount.

"What do you think you're doing?" Luke questioned furiously as he stomped over to the circle of future high school dropouts.

"Luke-" Jess swallowed and the man noticed the obvious drop of 'uncle' in front of his classmates, "I, uh..." the boy looked around sheepishly.

"I guess it's pretty obvious what you're doing isn't it? I could ask why you'd think this was okay, but I can answer that question too, you weren't thinking at all! And here I thought you were smart!" Luke let the anger take over, not registering the fact that the two had an audience and his nephew was shifting uncomfortably from foot to foot.

"Can we do this someplace else?" the teen finally asked in desperation causing Luke to halt his ranting upon hearing his nephew's hushed voice. His first instinct was to continue chewing the boy out no matter how uncomfortable he appeared to be, but one glance at the kid who looked embarrassed to even be asking that question in front of the crowd, he instantly felt pity and he found himself giving in to the compassion.

He sighed, "C'mon," he finally ordered, grabbing the teen's upper arm and pulling him from the group of onlookers. The looks of amusement on the other kids' faces as they passed told Luke he had made the right choice.

Luke walked quickly, Jess struggling to keep up as the uncle steered them in the direction of their house. The boy was quiet and his cheeks were still flaming from the entire situation, but Luke left his pity back at the school. Now that they were alone again, he could feel his anger reignite and he mentally coached himself to calm down during the short walk back to the house.

Once they reached home, Luke walked the boy up the stairs and through the door, hand still resting on the boy's shoulder, though more loosely now.

"Babe?" Lorelai called upon hearing the door open, "What are you doing home so ear-"

She stopped suddenly when she noticed the additional presence standing beside her husband.

"What are _you_ doing home so early?" She rephrased her question, now directed at Jess with an eyebrow raised. By the look on the kid's face it didn't take a genius to figure out something had happened.

"Jess, go to your room. I'll be in to talk to you in a bit," Luke ordered in an even tone.

Jess, glad to be sent away from the tense situation without having to explain himself, quickly moved his legs across the living room and disappeared through his door, closing it behind him. Once the door clicked shut, Luke motioned for Lorelai to follow him into the kitchen.

"What happened?" Lorelai asked once more regrettably.

The man shook his head, deciding on the best place to start, "The principal called today and asked me to go in for a meeting," Luke divulged.

"Oh no... what did he do?"

"Nothing actually, well not nothing," he rephrased, "but the meeting wasn't about what he did."

His wife shot him a confused look and he continued, sitting down at the table. "Turns out they did some standardized testing a few weeks back and I guess Jess tested off the charts."

"Really?" Lorelai smiled, "I mean not that I'm surprised, we know how smart he is."

"Yeah, well apparently they think he might be _too_ smart for Stars Hollow High. They think that the reason he has no initiative in school is that he's bored, the classes aren't challenging enough."

"That makes sense," Lorelai agreed, "So what does that mean?"

Luke sighed, "Well, they think that he should transfer to Chilton in the fall. Said they sent his test scores over already and he has a place if he wants it."

Lorelai's eyes went wide, but a smile danced on her lips, "Are you serious?" She questioned in amazement, "Rory hasn't even heard back about her spot yet."

"I know," Luke shrugged, "I guess this testing was sort of a big deal."

"This is amazing! What does he think about all this?"

The man shook his head slowly, tired eyes meeting his wife's.

"Well I haven't exactly had the chance to tell him yet," Luke sighed, "While I was at the meeting they mentioned that one of the benefits of him transferring might be he is less bored and therefore has less absences. Turns out they were about to call me about all his missed classes, but when they found out about the test scores they decided to just meet with me instead."

"So he's been skipping school?" Lorelai huffed in disappointment.

"Yeah, well then on my way back to the diner after the meeting I catch our little genius, not only skipping class, but with a cigarette hanging out of his mouth. I'm not joking Lorelai I saw red."

"You're kidding me! He was smoking!?" the woman's faced etched into a deep frown.

"It terrified me, I swear my heart stopped," Luke confessed.

"Aw Babe, I can only imagine after losing both parents to cancer," she gave him a sympathetic look as she rubbed his arm, "What did he say when you caught him?"

"Not much really," Luke shrugged, "I yelled, he asked if we could talk about it somewhere else, I took pity on him and brought him here and sent him to his room. That's as far as I've gotten so far."

"Well, just because we found out he's a little Einstein today doesn't mean we're going to let him get away with all this, right?"

"Definitely not," Luke shook his head firmly, "I should probably go in there and talk to him before Rory gets home."

Lorelai nodded in agreement, "Do you want me to come with you?"

"No. I caught him, I can deal with it," Luke promised, "You probably need to get back to the Inn anyway."

"I can wait until you're done if you want. If you need to go back to the diner after I can stay with him," she offered.

"It's okay, I think I'm home for the day now," the man sighed, "go ahead, I'll see you later tonight."

He pressed a kiss to her forehead and she squeezed his arm reassuringly before he turned toward Jess' room.

Though he didn't feel the boy necessarily deserved it, he knocked twice on the door, letting the boy know of his presence before letting himself in without awaiting a reply.

The teen was sitting on his bed when Luke entered, back resting against the headboard and legs casually pulled up to form an upside down V. He didn't say anything at his uncle's presence, instead watching in silence as the man slowly walked across the room and grabbed the desk chair, pulling it over to the edge of the bed and depositing himself into it.

Once settled in the chair, Luke looked up tiredly at the boy and sighed.

"What were you thinking Jess? Is it a stress thing because I promise if you're stressed we can find a better way-"

"I'm not stressed," Jess huffed in frustration.

Luke held his hands out in question, "Well then what?"

"I don't know," the teen shrugged, looking anywhere than at his disappointed uncle, "It was just something to do."

"Something to do," Luke repeated more to himself, shaking his head, "Seriously Jess? Something to do?"

"Can we please just drop it?"

"No we cannot drop it, you skipped school, I've now learned not for the first time, and I catch you not only not in class, but smoking, and you expect me to just ignore it and pretend it didn't happen?"

When the teen remained silent the uncle went on, "We've had the smoking conversation Jess. I know I've stressed to you how bad it is, how harmful. Jeez Jess, both my parents died from cancer and I can't begin to think what I'd do..." he cut himself off abruptly taking a breath. Getting himself all emotional was not what Jess needed right now. "I don't need you starting a habit that you can't quit."

The man could tell that the emotion behind his words, whether he meant to show it or not, had struck a chord with the teen, who even bothered to look guilty.

"I wasn't- I didn't plan on getting... addicted, or anything," Jess huffed, probably realizing how foolish it sounded himself.

"Do you think anyone actually _plans_ to get addicted to nicotine Jess? One cigarette is all it takes sometimes," the man sighed, scratching the back of his neck, "How many times has this happened Jess? Huh? Are you already addicted... or-"

"It was the first time," Jess cut the man off, "I barely took two puffs, I swear."

Luke nodded, hearing the frustration in the boy's voice, "Okay. I want you to promise me it will be the first and last time Jess. I don't care about peer pressure, I don't care that you're bored. You say you're not stressed, but if you were we would find a way to deal with it. You only have one body and I'm not going to watch you harm yourself."

"I won't."

"I'm serious Jess. You promise me stuff that you don't always keep, but this is a big one. If I ever catch you with one of those in your mouth again you won't be a happy kid I can promise you that."

Jess sighed, "You don't have to threaten me, I won't do it again."

"I don't mean to threaten you, I don't _want_ to threaten you," Luke shook his head, "I just want you to realize how serious I am."

"I get it, I do," Jess promised, "I didn't even want to smoke the stupid thing in the first place."

"I seem to remember peer pressure getting you into some pretty massive trouble when you were younger too," Luke reminded.

"It wasn't peer pressure. Those guys didn't care if I took one or not," Jess confessed.

Luke was confused now, furrowing his brow, "So you didn't want to smoke it and they didn't pressure you to smoke it, yet I still catch you smoking? I have to admit I'm really not understanding kid."

Jess huffed, growing increasingly frustrated with himself or Luke, the man wasn't sure, "I just... did it, I don't know. I guess you're right, I wasn't thinking."

Luke nodded, allowing his nephew's explanation to slide. He briefly wondered if it was just the sort of rebellious behaviour Mrs. Truly had been alluding to during the meeting.

"Alright. Whatever your reasoning was, I think we've come to the agreement that I don't have to worry about you doing it again, correct?"

The boy nodded once and Luke nodded back.

"You're grounded for two weeks starting now. One for smoking and one for skipping, which we will discuss in a second. That also means forfeiting all your shifts at the diner."

"What!?-"

"I don't want to hear it Jess," Luke warned cutting off the boy's complaints.

"Don't normal parents usually make their kids work _more_ when they're grounded?" Jess questioned unhappily.

"Oh don't you worry kid, there will be plenty of work for you to do at home, for no pay. You're going to be helping me out with that nice long list Lorelai has for me on the fridge, not to mention yard work, cleaning rain gutters, we can even see if Babette has any jobs she needs done and I swear if you roll your eyes at me one more time I'm going to tack on another week."

Jess huffed, but sank into his pillows once more, resting his back on the headboard.

"Now the real reason for this discussion, I want to talk to you about why your principal called me in for a meeting today," Luke started. He wasn't exactly sure how he was going to bring up the Chilton topic, mostly because he wasn't sure how Jess would react. On one hand, Luke felt relief in thinking that maybe this could be exactly what Jess needed to get him more engaged in school, more willing to do the work. But, on the other hand, the uncle was fully aware of how much Jess seemed to dislike school right now, and trying to convince him to agree to attend a school that will be even more work seemed like a tough sale.

Jess huffed, "I know skipping is wrong. I know I need to be in class. I won't do it again, okay? We can skip the lecture."

"I'm glad you know all that, Bud, and yes the topic was brought up, but that's actually not what the meeting was about," Luke informed.

Jess sat up a little straighter, racking his brain for any other misdeeds, "Well, then what? I honestly don't know what else I did Uncle Luke, seriously!"

The uncle shook his head, smirking a bit at his nephew's sudden seriousness, "You didn't do anything, Bud. Do you remember that testing you did a few weeks back?"

The teen nodded slowly, "Yes, but they didn't even let you study for that test Uncle Luke, if I did badly-"

"You didn't do badly," Luke assured, "Actually, kid, you sort of did the opposite of badly."

Jess looked caught off guard, "Really?"

"You scored off the charts, Jess. They actually said that possibly the reason you have felt so bored and have been skipping classes was because you weren't being challenged enough. Do you think you'd agree with that statement?"

Jess shrugged self-consciously, "I guess... yeah, you could say that."

Luke nodded in relief at hearing the admittance, "That's good. That's good, Jess. I know that since you were younger you've been complaining that the work was easy and you didn't feel like you needed to do it. I wish I had listened to you more back then. I should have been making sure you were getting something out of school and I didn't."

"It's fine," Jess bolstered, "I mean it's not like there's much we can do about it anyway, right? I'm not skipping a grade if that's what you're asking."

Luke quickly shook his head, "We're not asking you to skip a grade. Actually they had a very interesting proposition for you."

"Oh yeah, what's that," the boy asked jutting his jaw out while fiddling with a loose thread on his blanket.

"Well..." the man took a breath, "They were thinking that it might be beneficial if you didn't attend Stars Hollow High next year."

Jess raised his eyes towards Luke at that statement, taking a moment before he spoke again. "And just where do they think I should go?"

He sounded skeptical and Luke knew that this wasn't going to be as easy as it sounded. Sighing heavily, he looked his nephew in the eyes, "Your principal sent your test scores away to Chilton and they have a spot saved for you in the fall."

"Luke-" Jess began to protest.

"Listen, they just have it saved, Jess. We don't need to give an answer right away. They said it's there if you want it, they told me to go home and discuss it, but I really think this could be a good thing, Bud."

"What, to go to a school with a bunch of teacher kissing academic nerds and wear school girl uniforms? Seriously!?"

"I'm pretty sure they have pants for the boys," Luke attempted to make light, but the look on the boy's face told him it hadn't worked. Dropping the charade, Luke's smile faded and he sighed, "Look Jess, I just want you to think about it, that's all. I know you don't like school, but Chilton's going to challenge you. You're not going to feel bored. I don't care if your grades aren't exceptional there, but it would make me feel better to at least know that you feel more fulfilled at the end of the day. Would it hurt to try it for a few months at least? Or just go to an open house and see what it's like? We're going to be taking Rory anyway, what's the harm in looking?"

"Rory hasn't even been accepted yet," Jess spoke up, a hint of guilt in his voice.

Luke smiled fondly at the concern he had for his step-sister. Their bond really was something else. "The principal didn't seem all that worried about her getting a spot. He told me they haven't started accepting anybody for next year yet. Yours was a special case and they pushed it through early."

"Do we have to tell Rory before she finds out?" the boy questioned meekly.

"We don't have to if you don't want to," Luke agreed, "Although I think if you decide to tell her she would understand. She might even help you make a decision."

Jess shrugged again, silent now.

Luke squeezed his shoulder in comfort, "Just give it some thought, okay?"

The boy nodded once.

Luke paused for a moment before speaking once more, "I want you to know I'm proud of you, Bud. You may make me go grey sometimes, but you are pretty remarkable."

Jess smiled shyly, "Thanks."

He got up, feeling good about how the conversation went and mentally patting himself on the back.

"I want you to stay in here for a little bit though, you are supposed to still be in school after all. Just because you're a brainiac doesn't mean you're not still in trouble," he reminded the teen.

"I know," Jess nodded, "I'm sorry... about all that."

Luke smiled in reassurance, "One thing you can always count on is that I'll always forgive you, Bud. Just try not to take too many years off my life, okay?"

Jess smirked in reply, "I make no promises."

* * *

 **A/N- Yikes this got long and took forever to finish! Congrats to the person who guessed what the meeting was about ;) So what do ya think, could Jess be a Chilton boy? Let me know what you think! As always thanks for the feedback!**


	5. Chapter 5

April 2nd

"So, he liked the idea?" Lorelai questioned from the bed where she sat reading a magazine.

"Well he didn't outright say no," Luke clarified, pulling the sheets back to join his wife, "Although I had just punished him so he could have just been burying the hatchet for now."

Lorelai shrugged, "I don't think I've ever seen Jess be outspoken. I'm sure if he didn't at least plan on considering the idea he would have let you know, no matter how much trouble he was in," she pointed out.

"You're probably right... I just think this could be a good opportunity for him, y'know? I know I wouldn't worry as much."

His wife smirked, "I don't know if I would ever put you and 'not worry' in the same sentence."

A smile danced at his lips, "Okay, well I wouldn't worry about the school stuff as much at least. That kid's always going to worry me."

"Giving my man all these grey hairs," Lorelai agreed, playing with his locks, "We may need to get you some old man dye pretty soon."

"There's not that much," he swatted at his wife's hand.

"Aw Babe, don't worry, I like a man with a little salt and pepper."

"Gee, thank God for that..."

Lorelai smiled, but after a moment she sat up straighter and gave her husband a serious look.

"Okay, back to the seriousness. Jess is accepted to Chilton, he hasn't said yes, but I think if we have our way he will be going one way or another."

Luke nodded, listening to his wife.

"And we're going to find out about Rory within the next week or so, right?"

He nodded once more, "The principal said she's as good as in, though."

The woman nodded, yet Luke detected an apprehensive smile playing on her face.

"That's great, our kids are super smart and that's great," She paused a moment to collect her thoughts and Luke looked over when she didn't continue, "Babe, how are we going to pay for tuition times two for three years on top of saving for their college?"

Luke sighed long and even. He wouldn't lie, the thought had crossed his mind more than once since he had spoken to the principal. Chilton wasn't a cheap school. In reality, they might as well be paying for an extra three years at Harvard, or Yale or wherever else the kids might decide to go. The diner did well, but Luke wasn't a millionaire because of it, and though Lorelai had recently gotten a raise at the Inn, it still didn't mean the pair was swimming in extra cash.

"We'll just have to figure it out" he admitted, "I was thinking about maybe dipping into the inheritance from my parents."

"You still have that?"

"Well a few years ago when I turned thirty the bank called me to let me know the money my parents left to me had finally been released. I guess they had a clause that I would get it upon the completion of college or once I turned thirty and well since... Anyway, I didn't think much of it. I was fine at the time, it was just me and Jess. So, I never touched it. I'm not sure exactly how much it is, my dad left me his business after all, but maybe I could set up a meeting with my bank tomorrow and see where that gets us."

"That's a good start," Lorelai agreed.

"Yeah. It probably won't be enough, but it'll hopefully help," Luke shrugged.

"If worst comes to worst there's always my parents," Lorelai nearly whispered, looking pained to even suggest it.

Luke looked at her with doubt, it wasn't even a possibility, "We didn't even invite them to our wedding."

"I know... I know. I'm just saying if it comes down to that. God knows I don't want to see them since the last time they had us over for dinner. If they can't accept all of us then I don't want them to get any. But if it's for Rory and Jess' education... I don't know, it's just an option."

"Worst-case scenario," Luke agreed.

"The very worst," Lorelai nodded.

"Just let me see how the meeting with the bank goes and we'll go from there."

"Let's just agree not to mention any of this to the kids," Lorelai suggested, "They're going to feel guilty and I don't want this issue to be a deciding factor on if they go or not. Especially if I have to ask my parents."

"Worst-case scenario," Luke repeated.

"Worst-case scenario," Lorelai sighed.

* * *

Jess rolled over in bed that night. He hadn't been tired. Spending the afternoon in his room with nothing to do had caused him to have an unnatural amount of pent up energy and now that he had finally convinced himself to turn off the lights, his mind was far from ready to go to sleep.

The day had been tough. From the moment he had walked into school that morning he had known he didn't feel like being there and even with the knowledge that a riveting documentary on the decaying of a frog was planned for fourth period, somehow the promise wasn't quite enough to keep Jess' mind from wandering to what he could be doing if he wasn't cooped up inside.

Against his better judgement, the boredom had won out and after a lunch spent with Rory, Lane and Peter, he found himself sneaking out the back entrance of the school like he had done many times before. Rory would be mad, but at the time he didn't care, she wasn't a snitch after all.

Unfortunately, he hadn't planned on sealing his fate himself.

He had noticed the guys behind the building many times before, Jess wasn't the only student with the habit of skipping after all. Yet, today, Jess found himself in a somewhat social mood, and knowing that his bridge wasn't as safe as he used to think, he found himself engaging in a conversation with the guys as he passed.

The offer of a smoke hadn't been expected. However, the guy looked like he couldn't care less if Jess indulged or not. Jess had made nice with them, and it was just their way of offering a camaraderie between the teens.

He knew it was dumb, he knew it was stupid, he knew Luke would blow a gasket if he found out, yet for some reason, Jess' hand went for the stick and a second later passed it over for one of the other guys to light. Was it curiousness? Boredom? He wasn't really sure, but he wished now that he had taken a few extra seconds to think rationally before accepting.

Luke had shown up not ten seconds later and Jess could honestly say that he had never felt quite as embarrassed as he had at that moment. He should have known that his luck was running out the other day when he had almost been caught by Lorelai and he kicked himself for not playing it more careful after that, especially considering he was standing just around the corner from the diner this time.

He had deserved the lecture, but he was incredibly grateful when Luke had agreed to bring him home instead of continuing their public display in front of the boys who Jess didn't think he would ever be able to show his face to again, despite the unspoken respect they had appointed each other a moment before.

Really the lecture at home hadn't been that bad, far calmer than Luke was capable of. The two-week grounding had been a buzz kill, even if he should have seen it coming from the moment he started to skip classes.

It was the Chilton talk that had been unexpected. Jess would never have considered himself a brainiac. Of course he knew he was more educated than a lot of the students simply from the knowledge he gathered in his books, but to put a label on it made Jess feel odd.

His first reaction was a flat no. He couldn't picture himself in the uniform, much less doting down the halls and brown-nosing the teachers. He also knew from the pamphlets they had sent home for Rory that the workload was near double what Stars Hollow High enforced on them. Why would he willingly sign himself up to do more work when all these months he had been skillfully avoiding doing any at all?

Rory. That was another factor. She had come in to see him when she had gotten home from school, more to scold him than an actual visit and he just didn't have the heart to bring up the Chilton subject, even if he had been dying to bounce the idea off of someone who wasn't Luke. She hadn't even been accepted yet and Jess couldn't begin to think of how she would feel if he went to Chilton and she didn't. He wouldn't do it, it was as simple as that. He couldn't do it, not to Rory who wanted more than anything to attend the prestigious palace in hopes of it sending her off to her dream college in the end.

He tossed in his bed once more, breathing out in frustration and making the bangs that had fallen to his forehead dance from the breeze. The decision was impossible, and he feared he wouldn't get much sleep until he decided.

* * *

April 3rd

Jess exited the bathroom the next morning after finally managing to get his hair to behave. He didn't know why he had decided to put so much effort into his looks when he wouldn't be going out, yet he had only remembered he couldn't go anywhere about halfway through the styling session and he wasn't about to leave it half done.

Luke and Lorelai had both left for work early. Luke for the Saturday rush at the diner, and Lorelai who usually stayed home on weekends was putting in extra time for a wedding that was to be held at the Inn the following day.

He met Rory in the kitchen, both with the search for breakfast on their minds. Rory was already sat down munching on a pop-tart and Jess grabbed for his cereal before joining her at the table.

"So are you going to tell me why Mom and Luke were being so secretive this morning?" The girl questioned after she swallowed her mouthful.

"Excuse me?"

"Mom and Luke. They were leaving this morning and I could hear them in here whispering," she clarified.

"Maybe they were whispering because they didn't want to wake us," Jess pointed out obviously.

"It was more than that," she sighed, trying to explain, "I hear them every morning from my room, this time it sounded like something they didn't want me to hear."

"I don't know," Jess shrugged lazily, "I think you're reading too much into this."

Rory shook her head determinedly, "They've been acting strange ever since I got home yesterday and I have a feeling it has something to do with what went on with you yesterday."

"And why would you think that?"

"Because I made out your name more than once. Come on Jess, was there more to what you did yesterday than you all are telling me?"

"No," he deadpanned. Hey, it wasn't a lie, nothing he did yesterday had been kept from Rory.

"Jess," Rory stressed, raising her eyebrow like Luke liked to do.

"Seriously Rory! Nothing else happened! I skipped, I smoked, I got caught. End of story."

"And Luke just happened to be going past the school right in the middle of the busy lunch rush?"

Jess let out a loud groan, "You're not going to let this drop, are you?"

"Nope."

"Fine," he surrendered. He took a moment to search for the right words. The ones that wouldn't upset his sister. The ones that would let her know he was not going to do anything without her, that she was as good as in anyway, that she deserved it way more than him. This was not how he wanted to let her in on the news. Preferably it would happen once he had his mind made up, once he knew whether the girl had gotten in or not as well.

He sighed in frustration, "Luke was going past the school because the principal had called him in for a meeting."

"About the skipping?" Rory guessed, furrowing her brows.

He could have easily lied, went along with her guess and told her the truth when the time felt right, but this was Rory. For some reason it was a heck of a lot harder to lie to her, especially when she directly asked him for the truth, "It was about the testing we did, remember?"

"Yeah," Rory spoke slowly.

"I guess I did pretty well or something," the boy shrugged like it was no big deal.

"Pretty well? What exactly does that mean?" she pressed further, causing her brother to grow more frustrated.

"Ughh I don't know, I scored high, okay?... Like, highest in the school..."

A smile broke out on the girl's face, "You did!? That's awesome!"

"Yeah, well..." the boy shrugged once more, feeling embarrassed all of a sudden.

"Wait, this is good news, right? What's with all the secretiveness?"

"I..." He sighed, he was already in this deep, "They told Luke that I wasn't doing the best in school. Everything that you already know and have been harping me about."

"I told you with brains like yours that you should be doing way better!" she smiled.

"Yeah, well I guess they noticed that my grades and test scores didn't quite match up. They think I'm not being challenged enough."

"I believe that," Rory nodded, feeling proud of her brother, "So are they going to get you harder material or something?"

"Not exactly," Jess fidgeted, causing concern to grow on the girl's face.

"Jess? What's wrong? What do they want you to skip a grade or something?"

He looked at her with a frown and she looked back expectantly. He groaned loudly, shaking his head.

"They want me to go to Chilton, okay?"

If possible an even bigger smile grew on her face, "Jess that's amazing! If we both get in we'll be there together! I'd feel so much better knowing that you were there with me!"

"Yeah, actually Rory that's the thing... I sorta already did get in," he refused to meet her eyes, but her excited chirping quieted down and he feared the worst.

"You... oh. I didn't know they already sent out the acceptance letters."

He could hear the deflation in her voice. Her dreams were disappearing before her eyes and Jess needed to quickly reassure her, "No, no they didn't! Seriously Rory, nobody's been accepted, the principal says your chance is extremely high!"

Her eyes met his, "Really? Well then-?"

He shrugged in frustration, "I don't know! I guess the test was sort of big deal and they went ahead and gave me a spot. Seriously Rory I'm sorry! If anybody deserves to go to Chilton it's you not me!"

"That's not true," she replied softly, shaking her head.

"Yes. It is," Jess assured, "And if you don't get accepted, which you will, but if you don't I'm giving up my spot to you."

"No you're not Jess! This is important for you too!" she practically yelled.

"I don't even think I want to go!" Jess admitted, "I mean seriously Rory, can you picture me attending a place like that?"

"I told you weeks ago that I think you could," Rory reminded.

Jess shook his head hotly, "It just doesn't make sense."

Rory sighed, "It does. I'm not going to lie it does kind of hurt to know that you have a spot and I still have to wait and see, but Jess... maybe this could be a really good thing for you. Maybe it's just what you need to prove to you that you can do more."

"Oh here comes the pompoms," he rolled his eyes.

"No pompoms," she shook her head seriously, "I've been telling you for years that you can do more and finally someone besides me is realizing it too."

Jess sighed, eyes fixed on a spot on the floor, but not saying anything.

Rory stood up and grabbed the garbage from her breakfast, "I think you should think about doing it Jess, whether I get accepted or not."

She turned to leave and Jess waited until she was out the door to let out the breath he was holding. How was she always able to see reason in everything?

He looked around the now empty house, a whole day ahead of him and nobody to share his company with. He wished someone else was home to occupy his time so that he wasn't just stuck with his own thoughts all day. Suddenly his brain was too loud and he was growing tired of the back and forth up there.

Luke had left him a list of chores for the day, tasks that Jess hated and he didn't have the slightest urge to get done, yet in an attempt to silence his thoughts for a while he begrudgingly got up from his seat and grabbed the handwritten note tacked to the fridge door, reluctantly getting to work before he returned to his senses.

* * *

Luke walked into the house, catching the tail end of Jess hastily turning off the TV. He shook his head as the boy quickly settled back into the couch with a textbook of some sort turned to a random page and reading far too intensely.

He approached the back of the boy's head which was peeking over the back of the couch and tapped his hair gently.

"I'm going to pretend I didn't just walk in on my nephew playing video games while grounded and you're going to follow me into the kitchen, I want to talk to you," Luke spoke, raising an eyebrow.

"I wasn't-" Jess went to defend himself, but one look from his uncle told him it was a lost cause, "Fine," he sighed, dragging his feet in the direction of the kitchen. "For the record that game was helping me with a school project," he went on as he rummaged through the cupboard, grabbing a handful of dry cereal before sitting himself down at the table, "What better way to write a report on the war than to live it firsthand, am I right?"

"Oh I'm sure that game is a perfect depiction of World War I," Luke agreed sarcastically, "Besides, according to your History teacher you don't seem to need any help in that subject. I'll lock up those games if you don't plan to follow the rules when no one's home."

"Okay, okay, jeez," So much for pretending he didn't see it, the boy thought of his uncle's lie, "Do you actually have anything to talk to me about or can I go back to sitting in the living room staring at the walls like a good boy?"

"Rory stopped by the diner earlier," Luke informed and Jess nodded, "She said you guys talked."

"Yeah," the teen shrugged, "She practically beat it out of me, I didn't really have a choice."

Luke smiled, "I'm glad you told her. She really is excited for you. She was worried she hadn't shown it enough, but she was really happy about it."

"She alluded to such," Jess replied easily.

"So, does this mean you've given it some more thought today? Are you any closer to making a decision?"

Jess sighed, he really was tired of talking about it, of thinking about it, "I don't know Uncle Luke, I still don't see it working out for me."

"I know you have doubts Jess, but you have to understand at least a bit of why we think it might be a good idea?" Luke could tell the boy was losing patience and it was true the topic seemed to be on everyone's mind, but he knew that sooner or later they would have to make a decision.

"I just don't know if it's something I want to do," Jess reiterated, "Can we just stop talking about it for a bit?"

"Okay... yeah. I just wanted to ask you, Principal Merton called again last night, I was going to tell you, but I figured I'd give you the night to sleep on the idea before bringing it up."

"What did he want this time?" Jess snarked.

"He just wanted to remind me that he had scheduled an open house for Rory in two weeks and he wanted me to give you the option to go with her, you know, just see the school, see what you'd be getting into. I told him I'd ask you before I agreed. Do you want to go?"

Jess shrugged, "Sure," he replied, if not only to get the man off his back for a few days.

"Yeah?" Luke couldn't help but smile.

Seeing his uncle's expression Jess was quick to follow up, "That doesn't mean I'm going or anything, it just means I'll... you know, look."

"Of course, we'll just take a look," the uncle was quick to agree, but the smile that was now plastered on his face nearly caused Jess to roll his eyes once more.

"So..." Jess went on, "That wall isn't going to watch itself."

This time Luke was the one to roll his eyes, "Go, be bored, maybe I'll give the wall a paint job later so you can watch the paint dry for a bit," he joked dryly.

"Gee that would be terrific," Jess bit back but smiled as he exited the room.

* * *

 **A/N- Thanks for your reviews as always. It was a tough week for me, my guinea pig died suddenly and it was the most horrific thing to watch happen, hence even though I had this chapter ready I had no motivation to post it. It may take me a little while to post again since I'm still not feeling 100% about everything and have been finding it hard to concentrate on things but it will be up eventually!**

 **My brother and I are actually taking a road trip tomorrow to see one of Scott Patterson's coffee shop shows. We debated for a while if we even felt up to still going but we both have decided that it might be good to get away for a day so we're going to go. Hopefully finally meeting Luke after all the complications of trying to meet him before will lift my spirits a bit...**

 **Thanks again for all your support with this story and any thoughts on the chapter are greatly appreciated!**


	6. Chapter 6

April 16th

Jess cracked his eye open and after a split second of dread he remembered what day it was. Not only was it the last day of his grounding, but he was also getting the day off from school thanks to the Chilton open house that was happening in Hartford that afternoon. Both Luke and Lorelai were taking the day off as well and the family had planned to head into Hartford for lunch with Bud and Maisy before heading over to check out the school that hopefully both Rory and Jess would be attending in the fall.

Not that Jess was particularly eager to take a tour around the school, knowing full well the dreams both Luke and Lorelai had for him choosing to attend the prestigious palace. He knew if he decided he didn't want to go it would be a heated discussion full of disappointment from the elders that would end with Jess wanting to crawl in a hole and never come out. He knew his parents just wanted the best for him, but he hoped that in the end they really would let him make the decision for himself and not push him too hard to do what they wanted.

Luke was so sure that this school was going to be a great thing for him, and maybe it was. Jess just didn't know if he was prepared to rise to the occasion. He may have been bored and just getting by at his current school, but he was comfortable. He didn't have to work hard, he didn't have to push himself. He could slide under the radar and yeah maybe he missed a few classes here or there, but at least it wasn't a big deal. He was sure if he decided to skip a class at Chilton the work he would miss would be equivalent to missing a whole week. His days of slacking off would definitely be history, much to Luke's pleasure Jess was sure.

Sighing Jess rolled out of bed, happy that he technically got out of his last day of grounding a day early thanks to their outing. He had been going nearly insane being cooped up at the house before and after school for the past two weeks. Not only did he have nothing to do besides homework and chores to keep him entertained, but it only gave Luke and Lorelai ample time to bring the Chilton topic up at every possible chance.

The following week after Luke went in for his meeting with the school, Jess had started receiving separate work booklets from the rest of his class. Each teacher had been given directions to come up with ways to challenge Jess more in what would possibly be his last few months at Stars Hollow High and though Jess noted their effort, he still found that the new work wasn't that different from the previous. He didn't blame the teachers, not really anyway. They were trained to teach 'normal' kids, no more than that and they had never signed up to making a curriculum for someone who didn't fit the bill of 'average.'

Still Luke had sat Jess down at the table every day after school for the last two weeks to do his homework, trying to catch a glimpse of this new program he and the school had set up. Eventually he caved and asked Jess about it, if he was happier, if he felt more challenged. Jess told his uncle what he knew the man wanted to hear. Yes the new work was better, sure he was lucky that his teachers had agreed to help him out for the rest of the year, no he didn't need any help (he was pretty sure that question was meant to be turned down anyway if the dumbfounded look Luke gave his equations was anything to go by.) He knew his uncle would rather hear the truth than have Jess lie to him, but Jess just didn't want to get into another bout of how much better Chilton would be for him. He wanted his uncle to feel okay with the idea of him staying at Stars Hollow High if that's what he chose to do.

Throwing on some clothes and checking that his hair wasn't a complete disaster to be seen by his family with, he exited his room to get some breakfast. Rory was already sitting at the table practically vibrating with excitement for the day ahead. She still hadn't heard word back from the school on whether she was accepted or not, much to Jess' dismay, but she was still holding out hope and just as eager as ever to see the school she had been dreaming of.

"Can you believe it's finally today!?" she questioned her brother, looking more like a little girl awaiting Santa Claus, "I just can't believe we finally get to go see the school. I mean the pamphlets were great and all, but to actually set foot there. Did you know the banister was donated by Robert Frost?"

Jess was used to the girl's ramblings when she was overly excited about something and he knew that in these situations it was better to not bother trying to answer any of her questions until she was done.

"And Thomas Edison ceremonially lit a sconce on campus! Thomas freakin' Edison! Just the thought of walking through such a historical place is unbelievable."

"Well you're going to be able to walk through the school every single day for the next three years so maybe you could pause your party for a second and tell me where Luke put the rest of the pancakes."

"You don't know that for sure. I'm not in yet, remember?" Rory huffed at being reminded of the fact.

"You're going to get in so just stop," Jess rolled his eyes, guilt resurfacing at the knowledge that he was already accepted, "Pancakes?"

"Do you really think so? Principal Merton said that we should be finding out next week who got in and I guess I'm just getting a bit nervous. I mean maybe going on this tour today is a dumb idea."

"It's not. I swear Rory you're going to that school one way or another, so just enjoy the day, okay? You've been talking about this for months."

Rory smiled, "You're right, I should just enjoy myself and quit worrying."

"Exactly. Now seriously sis I'm dying of starvation here," the boy spoke dramatically.

"He's keeping them warm in the oven for you. He and mom just went upstairs to change before we go," Rory informed him.

Humming his response, the boy made quick work of retrieving his breakfast and lathering it up with butter and syrup. He was halfway through his second pancake when the elders returned to the kitchen.

"Oh good, see Luke, Jess found his breakfast, it's fine," Lorelai spoke to her frazzled looking husband.

"I just wanted to make sure he got something to eat before we left, you slept in late," he spoke the second part to his nephew.

Jess shrugged, "Day off school equals sleeping in I think, at least for us normal folk," he cocked his head towards the still overexcited girl sitting across the table and rolled his eyes, earning him a playful smack to the head from the man.

"Well I hope you don't require too much primping today because we've got to get a move on."

"I suppose I can go for the whole rolled out of bed look," Jess shrugged, "I'm sure Chilton wouldn't care, right?"

Luke shot his nephew with a tired glare and Jess couldn't help but snicker at getting the reaction he was hoping for.

"If you boys are done annoying each other," Rory broke in with an eye roll of her own, "I don't want to be late!"

Lorelai bit back a laugh, "Sweets it's ten in the morning, we're not going to be late."

"Well you know how much Maisy and Bud like to talk!"

"The tour doesn't start until two toots, I promise we will get there in loads of time," The mother assured, pressing a kiss to the top of her daughter's head, "Jess go get yourself ready quickly and grab the tie that you promised me was wrinkle free last night."

Jess sighed dramatically, "I don't get why I have to wear a tie to this thing! It's not like I'm a student yet!"

Rory exhaled loudly, "Jess would you just listen for once in your life!"

"Hey, cool it Hun," Lorelai chastised lightly, knowing that her daughter just wanted everything to be perfect today.

"Just go get the tie and bring it to me to tie for you Jess," Luke instructed losing his patience.

With one more exaggerated eye roll, the boy dragged his feet out of the room to retrieve the ridiculous object, feeling like his family was already ganging up on him this morning.

A half an hour later the family was in Lorelai's Jeep on the way to Hartford, Jess with his foot propped up on the center console reading a book and Rory gazing out the window, too anxious to focus her attention on much else. Luke and Lorelai sat in the front, bickering lightly on the fastest route to their destination. The argument was one they had every single time they drove into Hartford, and all parties knew it was more of a ritual than anything else at this point.

"I'm just saying the highway may seem like it would be the fastest, but I'm telling you! The back roads get you there exactly two minutes and fifty-two seconds faster Luke!"

"Whether that's accurate or not, I'm not going to change my whole route for a possibility of being there a measly three minutes faster! It's pointless!"

"Fine, have it your way, just don't come crawling back to me when we get to Bud and Maisy and they tell you that the last pot-sticker was ordered three minutes before we arrived!"

"They're going to feed us whatever they want either way," Luke shook his head.

"Well you'd be pretty darn sad if pot-stickers weren't even an option, wouldn't you!"

"When have we ever even had pot-stickers at Sniffy's!? I don't even think they're on the menu!"

"When have you ever seen a menu there to even know that!"

Luke groaned loudly, turning up the radio in an attempt to drown out his crazy wife.

* * *

"There's my babies!" Maisy greeted arms wide to envelop Jess and Rory into a rough hug, "My smart, smart babies," she pressed kisses to each of their foreheads before finally letting them go, "I want you to tell me all about Chilton!"

"We haven't even been to see it yet Maisy!" Rory laughed as they were directed to their usual table in Sniffy's Tavern.

"Well then I want to hear all about getting accepted then! When will you find out Rory?"

"Not until next week," Rory shrugged shyly.

"I will be waiting eagerly by the phone for the good news!"

"Don't say that! I might not get in!"

"Of course you'll get in!" Bud assured, appearing from behind the kitchen door skillfully balancing four plates as he walked, "Hey kids, it's been too long!"

Luke shook his head that even after all these years Bud still referred to him as 'kid.' He supposed when you've known someone since they were born it was a hard habit to break.

"Yeah sorry, we meant to come out after Jess' birthday, but things have been a bit hectic," Lorelai apologized. They always tried to make visits a regular thing, but with everything going on in their lives they hadn't managed to see the pair since Jess' party. The last time they had visited Hartford Bud and Maisy had been away visiting Maisy's sick sister. Luke had refused to even stop by Sniffy's when someone else had been in charge of making the famous food. Nobody could cook like Bud, not even him.

"Well we're seeing you now and that's all that matters," Maisy smiled lovingly, "Now how about you my genius boy? I want to hear all about your acceptance!"

"Jess' acceptance story ends with him getting grounded so I'm not sure that's much of thriller," Rory snickered, teasing her brother and dodging his swat swiftly.

Maisy shook her head, "Luke I still can't believe you could ground this sweet, sweet boy," she tsked, cupping Jess face lovingly.

"I'm sure you could believe it if you saw him with the cigarette hanging out of his mouth, or hearing that your 'genius boy' was on the verge of _flunking out_ ," Luke stressed the last words with an eyebrow raise to his nephew.

"Oh stop pestering the boy, we all make mistakes," Maisy waved her hands, causing Jess to smirk at his uncle.

"He's always harping on me Mais," Jess tattled with dramatics.

"Honestly Luke it's like you were never a boy yourself," She shook her head, everyone chuckling at Luke's exasperation.

He shook his head, "I'm going to stop coming here if you're all going to gang up on me every time."

"Oh enough whining from you now," the lady waved her hand, "Come over here and give me a hug!"

Luke fulfilled the lady's request as they all settled down to enjoy their home-cooked meal, steering clear of any more talk that would make Luke's face turn that particular shade of red.

* * *

The family pulled up to Chilton just before two that afternoon and all four of them were instantly amazed by the size of the place.

"The pictures made it look... smaller," Rory observed.

"And less 'off with their heads,'" Jess added.

"Yeah," Rory agreed, giving her brother a nervous glare.

"Come on now, it's just a building," Lorelai encouraged, "I'm sure it's not half as scary inside."

"The architecture is amazing," Luke remarked.

"Sure is," Lorelai chirped, having no clue about anything to do with architecture, "Now are we all just going to sit here ogling or are we going to be on time for this appointment?"

"We better go in," Rory agreed, taking one last deep breath before opening her door.

The four walked up to the main entrance, wondering aloud exactly where they needed to go when they noticed a man walking across the courtyard towards them.

"You must be my two o' clock, Rory Gilmore and Jess Mariano?" The short older man inquired greeting the group.

"Yes, hi, I'm Rory," she introduced shaking his hand.

"Ah your grandma has spoken very highly of you Miss Gilmore!" The man smiled brightly.

"Wait. How do you know my mother?" Lorelai questioned instantly in defence.

"Oh I'm very good friends with both your parents. You're their daughter Lorelai I presume?" He questioned with a smile.

"Uh... ya I guess," she answered bitterly.

"Now, I'm sorry, how do you all know each other?"

"Jess is my brother," Rory spoke up determinedly.

"Oh. I don't remember Emily mentioning a grandson," the headmaster furrowed his brow in confusion.

"Of course not," Lorelai mumbled under her breath causing Luke to nudge her gently. She coughed a few times.

"Well actually Rory's mine, Luke is Jess' uncle and Luke and I just got married a few years ago, so we're kind of like a modern day Brady bunch," she attempted a joke.

"I see," the man furrowed his brow even deeper and Lorelai was no longer surprised that he was a friend of her parents, "I suppose we should start the tour then."

"Let's," Lorelai gave her best fake smile.

Jess who had been watching the whole conversation from the side sighed deeply as he followed the crowd. If Chilton wasn't bad enough now he finds out that it's run by the friend of the two people who seemed to hate him the most. He knew the school would be full of people like them, but the added knowledge did not provide brownie points for the place.

"This, of course, is the main atrium," Principal Charleston informed as the group walked inside the huge double doors.

Jess stood in amazement at the grand room. It definitely didn't look like a school to him. It reminded him more of the entrance to some of the big skyscrapers that were in New York. Jess remembered one night when he was younger and Liz had been gone doing who knows what. He had forgotten his key into their apartment and at nine years old he had yet to master the ability to pick a lock. He knew that sleeping in the hallway of their not so safe apartment building was out of the question. Instead, he found himself in search of a place in the city for him to sleep away from the cold November chill. He had found an office building with enough people in it that he could slip in unnoticed and waited for about an hour until the workers had gone home and the building had been emptied. Carefully he had crawled under the 'out of order' stall that he had been hiding behind and found himself a little couch at the far end of the hall to use as a makeshift bed. It was an odd place for a piece of furniture to be, but Jess had grown accustomed to the weird decorating habits of the famous city that he called home and instead he felt grateful for his somewhat soft sleeping quarters for the night. It had definitely beat sleeping on the park bench.

He shook the memory from his mind and try to refocus on what the older man was saying, amused when he heard the same 'fun facts' that Rory had been spewing that morning. He glanced at his sister and shook his head at her focus, like she had never heard a word the man was saying before.

"I'll take you to observe a ninth grade class for a moment if you like. The two of you will obviously be going into tenth next year, but the students that you will see here will be your peers if you choose to attend."

Quietly he ushered the four into the back of the room and Jess shifted uncomfortably when half of the class instantly turned to look. With a slight annoyance in her voice, the teacher called for their attention once more and the family leaned against the back wall listening to her lecture.

Jess admitted that the curriculum they were teaching sounded much more advanced than that of the ninth graders in Stars Hollow High and he watched as the students scribbled endlessly in their notebooks.

Feeling someone's eyes on him, he glanced near the front of the classroom where a preppy blond girl was glaring at them. He nudged his sister's side and jutted his head towards the stare.

"What's her problem," he whispered, causing the girl to shrug.

They observed for a few minutes longer before they were shuffled out of the room again with the promise of the cafeteria as their next stop.

By the time the tour was over Jess was sure he had seen every inch of the large building and he was exhaustively bored.

"Well that was insightful," he muttered sarcastically as they walked back to the Jeep.

"C'mon Jess, don't be like that. It looks like a great school," Luke sighed.

"It's an amazing school!" Rory agreed.

"It better be for these prices," Lorelai grumbled looking down at the pamphlet the parents had been given.

The pair shot each other a concerned glance, neither exactly sure where they would find the money, but both willing to do whatever it took. Luke shook his head, "All I'm saying is none of those kids today looked bored, did they Jess?"

Jess rolled his eyes, "I'm not bored!"

Luke groaned, "Don't even try to backtrack this one, we've had way too many discussions about this already."

"Yeah and I'm sick of it so how about I end them now and just say I'm not going!"

"You can't just say that," Luke shook his head.

"If you're not going to let me make the decision, then why are you even bothering to ask me?"

"Jess! I just want you to give this more than half a second of thought!"

"I have given it thought!"

"Not without already having an opinion formed in your mind!"

"You won't even consider my side of it!"

"That is not true and you know it!"

"Okay!" Lorelai finally broke in, "Why don't we all cool off for a bit guys. It's been a long day and we're all tired. I believe milkshakes on the way home were in the plan."

As Luke sat behind the steering wheel attempting to calm his annoyance Lorelai gave him a look from beside that promised that they would discuss the situation privately once they got home. Nodding slightly and knowing that Lorelai was right to diffuse the fight for the time being, he shifted into drive and took off in search for a satisfactory place for milkshakes.

* * *

Jess sat in his desk chair later that night, drumming his fingers on his unopened science book. Luke was still annoyed with him and since he still wasn't allowed to go out until the next morning he decided that it was safest to stay in his room for the evening, away from the gaze of a disappointed uncle.

He sighed as he picked up the Chilton pamphlet that had been discarded on the floor when he had gotten home. Begrudgingly he leafed through the information once more. He hated this feeling. He knew what the right thing to do was. He also knew what he would like to do. The thing he hated the most, however, was that he felt like he had no actual say in the matter. Jess did not do well when he felt like he had no control and that very feeling had been overcoming him for two weeks now. He groaned quietly, tossing the leaflet aside once more. He rested his head on the cool tabletop, closed his eyes and wished not for the first time in his life that he could be like everyone else. On top of the crappy hand he had been dealt in his life so far, why couldn't he have just been born average?

* * *

 **A/N- I'm back! Sorry everyone, I really didn't mean to take such a long break but August just ended up being a really busy month for me. I want to thank all the new readers for dropping reviews throughout this story and the last and letting me know that there is still interest here! This chapter was done a different way until I got a message that inspired a whole new storyline that I hadn't considered and I ended up changing everything up. I hope it was the right move! Anyway, I'm ready to get back into the groove of writing this and I hope you have all stuck around! Please review if you have a spare moment! Thanks!**


	7. Chapter 7

April 17th

"I must be seeing things, is Jess Mariano really out in a non-school setting?" Peter feigned shock as Jess and Rory approached him in the park Saturday morning.

As of last night, Jess had officially served his time on house arrest and when he had woken that morning he had wasted no time in getting away from the house that he had gotten to know all too well in the last two weeks.

"Yeah and I've got my first shift back at the diner at noon so let's go play some basketball or something," Jess urged, needing to blow off some pent-up energy.

From his side Rory rolled her eyes, "I can't believe Lane left me with you two all day," she complained, already bored with the boys' plans.

"Hey you could have joined Mrs. Kim's travelling choir too," Jess teased with a smirk.

"I think Mrs. Kim made the group specifically to get Lane away from my bad influence and all you unwashed boys."

"I still remember her face when she found out Luke and Lorelai were getting married and I'd be at the house every time you and Lane had sleepovers," Jess laughed.

"That wasn't funny! It took her nine months before she could finally be convinced to let Lane spend the night again," Rory frowned, remembering her past misery.

"Yeah well at least you can be seen around Lane!" Pete complained, "I still have to hide every time Mrs. Kim's within view!"

"Well letting her precious daughter near one boy is bad enough. It's going to take another ten years before she would even start considering letting you around. That is unless you can transform into a Korean doctor-to-be overnight," Rory pointed out.

Pete shrugged, "Maybe I'll find out I was adopted."

At that, the teens had made it the short walk to the basketball court behind the school. It was still relatively early and most of the kids that frequented the court were still in bed, leaving the place empty. Jess usually liked doing things without a crowd, however, basketball was one of the few activities he actually preferred when there were a few more guys around to make the game more interesting.

"I guess we'll play one-on-one," Pete shrugged, tossing his ball to Jess.

"That's not much of a challenge for me, though," Jess smirked, tossing the ball back to Pete.

"Excuse me! That's awfully big talk coming from you," Pete yelled back, throwing the ball at Jess' shoulder as Jess dodged it skillfully.

Rory read from the sidelines as the boys played and playfully yelled insults and profanities at each other on the court. It didn't take long for the match to intensify and Jess found himself getting lost in the game easily. It was one thing he loved about basketball; when he played he could forget everything. There was no stress about Chilton, or work, or disappointed parents, it was all about the game.

He was so lost, in fact, that he almost didn't notice another taller and lankier boy that he had never seen before approaching the asphalt, causing the heated game between friends to stall and Rory to look up from the book she had been reading. Finally another player to make things more interesting, Jess thought, waiting for the boy to get close enough to talk to.

The teen, however, did not approach to join the game. Instead, he crossed the pavement, smiling kindly at Rory, "Whatcha reading?"

"Uh," Rory blushed, fully looking at the unfamiliar boy for the first time and blushing a bit too obviously. Within seconds Jess was over at the bleachers to access the situation.

"You'll have to excuse Rory, she tends to zone out when she's in the middle of a good book," Jess explained, gaze burning into the boy as he tried to read him.

"It's fine, I think it's cute," he shot Rory another soft smile, causing her blush to deepen, "I'm Dean," he finally introduced, extending his hand out to the girl.

Rory stared dumbly at the hand, but her own remained unmoved.

"Jess, Pete, Rory," Jess interrupted the flirting and gestured to his friends, "Now if you don't mind, we have a game to get back to."

"Oh, do you mind if I jump in too?" Dean asked still not noticing Jess' obvious wariness of him, or choosing to ignore it.

"Two on one? It wouldn't really work," Pete cut in, reading Jess' defensiveness and hoping to have a more polite response than what his friend's might have been.

"Maybe Rory could play too," Dean offered, causing Rory to shake out of her daze.

"Me?"

"Rory, playing basketball?" Jess barked out a laugh, "I don't think-"

"Sure," Rory cut him off, "I mean, I'm not very good, but if it would even up the teams."

"I'm sure you're just fine, I can even give you some pointers if you want," Dean offered sweetly.

Rory smiled dumbly again, causing Jess' stomach to twist and as Pete and Dean passed, he shot his sister a dumbfounded look. Rory only shrugged in response, obviously still a bit embarrassed by her evident flirting.

Jess shook his head as he followed the other three back onto the court. He wasn't sure he liked the idea of his sister having a crush. Not one bit.

* * *

"Jess? Hey Jess, snap out of it!" Luke waved his hand in front of his nephew's face later that afternoon, "I know you haven't had a shift in few weeks, but that doesn't mean I won't send you home if you're slacking off. I've done it before."

"Sorry," Jess tried to look apologetic, though to be honest, he had barely registered his uncle's scolding.

"Are you feeling okay?" The man asked, now concerned by his nephew's reserved response. Not that he didn't appreciate the lack of smart remark from the boy, but it wasn't his nephew without one either.

"Fine," Jess huffed, "Didn't Rory say she was dropping by this afternoon?"

"I don't know, you were the last one to see her, bud," Luke shrugged, looking through his order pad, "It's only two. Didn't you say she was showing some new kid around town?"

"Yeah," Jess spat.

"Are you sure you're feeling okay?"

"Just dandy," Jess sighed.

Luke furrowed his brows at the teen's odd behaviour, but let it go, "Why don't you go wash a few dishes in the back, it's slow out here. Maybe the water will wake you up a bit."

Jess hated washing dishes, but he knew his bad mood was going to get him in trouble eventually if he didn't take the out, "Sure," he agreed, shrugging past the man towards the kitchen.

In the end, the duty was a great way to get his frustration out and picturing each dish as Dean's head really made for a pile of extra sparkling plates in the end.

Feeling better after finishing the task, Jess made his way back out to the front with high hopes that the rest of his shift would be brighter.

That is until the bell above the door chimed and an extra giggly sister walked through with the new kid in tow.

"Hey Rory and- oh," Luke greeted, eyes landing on her new friend.

"Luke this is Dean, he's new in town," Rory introduced.

"Uh, Jess didn't mention, I mean I thought, uh, hi," he extended his hand to the fifteen-year-old, "Luke Danes, Rory's step-father."

Jess watched the exchange, biting back a chuckle. At least he wasn't the only one with mixed feelings about the new kid.

"Nice to meet you," Dean nodded respectfully and Jess rolled his eyes at the act, "Hey Jess."

He gave a curt nod in response and as Luke looked from Dean to Jess, the teen was sure that his uncle had finally clued in to where his less than stellar attitude had come from.

"So, um, what can I get you two?" Luke finally asked as Rory chose a stool and gestured for Dean to take the one beside her.

"Well, I was telling Dean all about your amazing chili fries!" The girl smiled.

"Two chili fries coming up," Luke nodded, disappearing into the kitchen and leaving Jess alone in front of the pair.

"I took Dean to Andrew's Jess. He told me to let you know your order just came in. I would have got it for you, but you still haven't paid me back for the last ones," she rolled her eyes, but it was evident that she wasn't really mad.

"No, I kept my mouth shut about that stray cat you snuck into our old apartment last month and you said we were even!" Jess reminded.

"Jess! Not so loud!" Rory admonished, looking past him to make sure Luke was still out of earshot.

"Relax, it's not like it's still up there."

"No, but he's still trying to figure out why he sneezes every time he goes up there. I swear I cleaned every bit of cat hair!"

"That cat shed like crazy, you'll still be cleaning cat hair for at least ten years."

Dean smiled as he watched the exchange, "You two are good siblings."

"What?" Jess snuffed, nearly forgetting that Stretch was still there.

"I mean, I have a little sister, she's eight, and we're constantly fighting," Dean elaborated.

"Well, Jess and I were best friends before we became siblings, that probably helps," Rory shrugs.

Dean shook his head, "That's lucky."

"Yeah, well I better get back to work," Jess excused himself, feeling angry even though the boy had said nothing that should have caused it. Honestly, Dean seemed like a great guy, the kind that anyone would be proud to take home to meet their parents, yet Jess just couldn't shake the dislike that seemed to develop the second he saw his sister blush.

* * *

Jess was in the front yard working his frustration out through his basketball when Rory came up the driveway with a goofy grin still plastered to her face.

"Where were you," he accused as soon as he saw her, "I worked today and I still got home before you!"

"I got pizza with Dean, I let mom know," Rory frowned, matching her brother's.

"You spent the whole day with Dean," he said, more of a statement than anything else.

"Yeah, so?" she responded with a shrug, "He just moved here, he doesn't know anybody."

"So of course you take him right under your wing like a good little girl scout," Jess snapped.

"What is your problem! Dean's a good guy and you've been snippy with him since you first met!"

It was a question Jess didn't really know how to answer, but he was too heated to care, "I'm just saying you could do better."

"What do you mean 'do better?' We're just friends Jess!"

"Yeah? Your face has been mighty red all day and you've never been willing to play basketball when Pete has asked you," he shrugged coldly.

"I wasn't just going to let you leave him out. God Jess, you're acting like a mad person."

"Not as mad as you in front of jerk-face," he knew he sounded twelve at this point, but he was past caring.

"Ugh, just shut up, Jess!" Rory huffed, stomping towards the house.

"Going to write Mrs Rory Forester a hundred times in your diary!?" Jess yelled after her, but she didn't turn back.

Just as she reached the door, Jess on her tail, Lorelai opened it, "Hey, what's all the yelling about? You guys are going to have Babette on our doorstep."

Rory continued through the door, pushing past her mom and slamming her door faintly in the background.

"Jess?" Lorelai turned to him in complete confusion.

He shook his head in response, "It's nothing, forget about it." He promised, out of steam and tired. He passed the woman as well and disappeared through his door a second later, a softer click than the girl's as he closed it behind him.

Lorelai was left standing on the front step, unsure of what exactly just happened. It's not like the kids fought all that often.

As if on cue, Babette emerged on her front porch, "Hey Suga! Everything okay over there!?"

"Yes Babette! Everything's fine!" she waved her off, re-entering the house and closing the door. "Just a house full of teenagers," she mumbled the last part to herself, heading into the kitchen to make a strong pot of coffee.

* * *

April 18th

The next day Luke had taken Rory into Hartford on a supply run for the diner. She had still been upset and the parents had decided that both kids could use a one-on-one day with each of the adults. Lorelai was sure that by the time she got home Luke would have worked his magic and her daughter would be as good as new.

The pair had discussed the boy issue the previous night in bed. Lorelai hadn't actually seen the new kid, but from Luke's description he seemed like a nice enough guy once the shock of seeing Rory with a boy that wasn't Jess or one of his friends wore off. Neither of them were particularly ready for the young girl to start dating, but they both agreed that so far it seemed harmless and they would rather her tell them about it than forbid her and have her sneaking around. It was going to happen eventually. Jess had already had a few innocent crushes and at their age none of the relationships lasted very long anyway.

Jess. That kid was another story.

Honestly, Lorelai found it cute that he was so protective of his sister, even if he wasn't showing it in the most loving way. She understood where he was coming from and she knew eventually he would come around and get used to the idea, just as she and Luke would as well. The sulking in his room, though, needed to stop, and Lorelai was up to the challenge of cheering up the fifteen-year-old.

"Jess!" She called, rapping loudly on the teen's door, "Come on Jess! It's a beautiful day and I need your help with my errands!"

Hearing no response, the lady sighed and pushed the door open, not caring that she wasn't invited.

"Ok dude, come on, we're going to town!" she ordered, pulling the boy up from where he was lounging on his bed with a book.

"I don't feel like it, go without me," Jess mumbled, still trying to read the page while Lorelai was pulling at his arm.

"You're telling me that you've been stuck in this house for two weeks and now you're going to willingly spend the day in here?"

He gave the woman a tired look, knowing that she wasn't going to let up, "Why do you care anyway, it's Sunday, y'know the day of rest."

"I _care_ because I don't want to watch any kid sulking around the house all day and I'm scared that if I leave you all alone I might come back to Dean's head on a stake," she gave him a knowing look.

He didn't say anything for a while, hating that he was letting the whole thing bother him.

"We're not going to lose her because she likes a boy you know," Lorelai spoke up when he wouldn't.

"I don't care if she likes a boy, just... not him."

She laughed at that, "Ohhh buddy, believe me, no boy is going to be good enough."

He sighed in defeat.

"And no girl will be good enough for you either, kid," she added as an afterthought, "But I'm still going to let you date, okay?"

"Fine," he agreed, accepting that he may have acted a bit ridiculous, "That doesn't mean I'll ever like him though."

"But you'll be nice, right?"

His face pleaded with her, but she shot him her best 'mom look' in response.

"Maybe it would be best if I just stayed away from him altogether," he finally decided.

The woman laughed, shaking her head, "Kid, you're something else. What am I going to do with you?"

"I believe you were going to take me for ice-cream," he smirked in response.

"Oh... fine! But only because I want some too! You don't win this one bucko!"

* * *

April 19th

The weekend was over all too fast for Jess' liking, even with having Friday off. He and Rory still hadn't exactly made up and they hadn't spoken to each other since the big blow up in the yard. Lorelai's talk the day before had made Jess realize that he had been ridiculous and wrong, but he has also always been stubborn and he wasn't exactly ready to admit to the girl that the way he had acted might have been out of line.

Instead, Rory had spent the school day with Lane, and Jess was just fine with the company of Pete.

"I swear I'd love to punch him in that pretty face of his," Jess vented to his friend when they passed Dean in the hallway just before lunch.

Pete laughed, "You never would. Luke would be pissed at you for most likely getting suspended and Rory would probably never speak to you again."

"Well I can imagine it at least," he huffed in response.

Just as the boys were getting ready to head to lunch, Lane found them and Jess became concerned when she seemed to be rushing over to them.

"What's up with you?" he asked when she was in earshot.

The girl looked torn, but after a silent war with herself, it seemed that she gave in, "I know you and Rory are in some sort of fight right now, and she told me not to bother telling you, but I know you'd want to know, so I'm telling you anyway, because this fight you're in is dumb, and this is big news, and I know she'll want you to know either way and-"

"Lane!" he cut her off from her nervous rambling, "What is it?"

Composing herself she took in a deep breath, "Principal Merton wanted to meet with her during lunch about Chilton."

Jess felt his heart speed up for his sister, "Did he say if she was in or not?"

"I'm guessing that's what she'll find out in the meeting," she pointed out.

"Well, did he sound like it was positive or negative?" he pressed for details.

"It was a note."

Jess sighed, realizing if he wanted more info he'd have to go meet his sister. Leaving his two friends, he set off in the direction of the principal's office. Upon arriving he noticed that Rory was nowhere in sight and he concluded that she must already be inside. Catching his breath from the brisk walk, he took a seat in one of the chairs that lined the outside of the office and waited.

"Mr. Mariano?" the receptionist called when she noticed Jess taking a seat, "What did you do this time?"

"Nothing!" he responded annoyed that everyone always assumed he was in trouble, "I'm waiting for my sister."

He knew that Rory didn't want to speak to him at the moment, but it didn't stop Jess from knowing he had to be there for her no matter the outcome. She wanted this more than anything and fight or not he would be there to celebrate or pick up the pieces, whichever it would be. He just hoped more than anything it would be the former.

The meeting seemed to have gone on forever and Jess wished he had decided to eat lunch first when his stomach let out a loud growl involuntarily. Finally, after what felt like forever the door opened and his sister emerged, showing no sign of joy or sadness. As soon as she spotted her brother she stalked over to him.

"I told Lane not to tell you," she rolled her eyes without so much as a hello.

"Well, did he tell you? Are you in?"

"What do you care anyway?"

"Come on Rory, just tell me! I've been waiting out here forever!"

She stared her brother down for a moment before a small smile cracked through her face.

"You did it," Jess' face lit up, "You got in, didn't you!?"

"I got in," Rory confirmed, still trying to hold back her smile, but failing miserably.

"I knew it! I told you!"

"So this means we'll be going to the same school next year, right?" Rory pressed her brother, knowing he still hadn't agreed.

"Ugh not you too! Come on Ror this is supposed to be a happy occasion!"

"Yes and I'd be a whole lot happier if you'd just decide that you were attending Chilton once and for all!"

"Just drop it, Rory. Come on, I'll buy you a piece of celebratory pie, I'm starving!"

"Jess!"

"Rory!"

* * *

 **A/N- Just for the record, before I get into anything else, Jess and Rory are not going to have feelings for each other in this story. Jess' jealousy is purely due to the fact that he is protective of Rory as any brother would be. I know some people were still hoping that they would have a relationship in this and I hope you guys understand that since they grew up together it just wouldn't work. Hopefully nobody will be too put out by that.**

 **I was debating whether to have Rory get into Chilton or wait a couple months after school started for a position to open up for her, but ultimately I wanted her and Jess to attend the first day together and so it was finally time to make the decision.**

 **I hope you guys enjoyed this chapter and please review if you can! Seriously even a two word review would make my day! I feel like this story might be losing some of it's following. Thanks!**


	8. Chapter 8

April 19th

"So, this is a good thing, right?" Lorelai questioned as she lay in bed staring at the ceiling.

"It's a very good thing," Luke nodded from where he laid beside her.

Both parents were happy, thrilled for Rory even. When the kids had gotten home and announced the news to them, the family had celebrated wholeheartedly. Take-out for dinner, ice-cream and pie for dessert, happy chatter about the coming year filling the house.

Now though, alone in the darkened room, just the two of them, reality had set in.

"Are we any closer to figuring out how we are going to pay for two tuitions for the next three years?" the woman voiced the concern that was weighing heavy in the room.

Luke sighed, "You know I talked to the bank last month, my dad's money will really help."

Lorelai turned to her husband with a sad smile, "It will help for the first year Babe... for one of the kids."

His face dropped knowingly, "It's a start."

"Yeah..."

"Are we doing the right thing here?" he suddenly spoke up causing his wife to turn her head to him, "Should we not be forcing Jess to go? I mean we haven't even told him yet, so it's not like we would be giving him mixed messages. He doesn't _want_ to go Lorelai, and this is Rory's dream. I mean what if we just got Jess a tutor and..."

"He needs this, Hun, just as much as Rory. Neither of their educations is more important than the other and honestly, right now I think it's more important that Jess goes, even if he will fight us on that."

The man sighed, "I know, it's just..."

"We know what we have to do," Lorelai addressed the elephant in the room, but Luke shook his head determinedly.

"No Lorelai, we can make this work! I can cut back the help at the diner, take on more shifts and maybe if you-"

"Babe, we both already have massive workloads, we'd never see the kids. It's the only other option."

"I can't put you through that, I can't put the kids through that," he shook his head.

"It needs to be done. I'll get over it and the kids will be fine. We've discussed the fact that their education is top priority and I'm willing to suffer a little if it gets them where they need to be."

She paused for a moment taking a deep breath in, "Even if making a deal with the devil may seem like a better option."

They laid in silence for a few minutes, mulling over pretty much their sole option.

"They may be willing to help Rory, but they don't even acknowledge that they know Jess," Luke pointed out to the silence.

"It won't matter," Lorelai shook her head slowly, "I know my parents. They'll have me right where they want me."

"How should we do this?" he asked, accepting their fate.

She groaned, "My birthday's next week. I'm sure they'd be thrilled to see me for that. I'll set up the dinner. We'll send Jess and Rory out of the room and ask them then. I don't want the kids to know if they don't have to."

"They'll know something if we are willingly taking them back for a dinner there. It's been years since the last catastrophe."

"We'll think of something. They don't need that guilt over their heads."

Luke sighed tiredly, rolling onto his side and gazing at his wife, "I love you, you know that?"

"I'd say the feelings are pretty fifty-fifty," she smiled, leaning in for a lazy kiss. "I guess we have to have the _discussion_ with Jess soon."

"Yeah, I want to do that like a hole in my head," he muttered sarcastically, already imagining how the talk would go, "he's going to resent us for not letting him make the decision."

"I know, babe, but we'll deal with it. Sometimes we have to decide what we think is best for him and this is one of those times. Eventually he'll come around. He has to, we feed him," she attempted to make light.

"I hope so," the man mumbled tiredly.

The couple lay together in the dark for a long time. Both knowing that their brains would not be allowing sleep to overtake them anytime soon.

* * *

April 20th

4512\. That was the answer that Ms. Harper was looking for as she stared down the class. It took Jess all of thirty seconds to figure it out, but there was no way he was going to raise his hand to bring the woman out of her misery.

She had asked three times now for someone to give her the correct response with the request that she hear from someone new. He knew she wouldn't call on him. _That_ she had learned long ago would only end in suffering on both parts, but Jess still got irked every time any of his teachers used the age-old phrase, 'I want to hear from someone new!' Why were teachers always so happy to make their student's lives miserable any chance they got? Of course, he knew that Ms. Harper got joy out of everyone's misery no matter what, but still, if he was a teacher he would never subject his students to that kind of torture.

Rory nudged him from his right and he raised his eyebrow at her. She flicked her head towards the teacher and raised her eyebrow right back at him. Jess had to stop himself from laughing out loud at her suggestion, as if he would willingly participate in class. Rory, always trying to convince him to push himself. He gave his sister a long look before turning back towards the teacher without a word.

She looked like she was just about to lecture the students once more about the importance of participating in class when out of the corner of his eye Jess noticed a hand hesitantly rise from two rows over.

"29?"

Jess did let out a snort at that and a few heads turned in his direction including a warning glare from the teacher. Of course Dean would be the good little boy who participated in class. Of course he would also be the one to get the answer so completely wrong that it was embarrassing.

"Not quite Dean, but thank you for at least trying. The answer's 4512."

Jess continued to smirk as the teacher went back to the board to show the class just how she had gotten the answer. He turned to Rory once more, hoping that she saw just how smart her crush really was.

Unfortunately, as he turned his amusement was deflated instantly. To his surprise, Rory was staring at the new kid with a proud smile on her face and when Dean caught her gaze he smiled with a small shrug. Jess whipped his head forward hotly, the entire scene too disgusting to watch for another second.

He and Rory were on good terms again and he really didn't want to fight with her anymore, but watching the girl act completely foolish in front of this guy was ridiculous. Maybe Lorelai was right, maybe no guy would ever be good enough for his sister, but surely there was someone better than a moose-sized airhead out there for her. He was glad that Rory would be moving schools next year. Hopefully she would find a more complex guy at her new school. Although Chilton might not be any better for her, he supposed. Next thing he knew she would be bringing home some rich snob, who cared more about blowing his daddy's money than actually trying to connect with Rory. Then, he would be begging to have simpleton Dean back. Jess shook his head, deciding that the topic of his sister's love life was not a good topic for his wandering brain right now. He would have a panic attack before the end of class if he continued worrying himself over the subject.

Still, he paid no attention to the rest of the class, certain that he already had a much better grasp on the concept than the rest of the class and knowing that his homework that night would be no issue at all. Instead, he let his mind wander to some safer topics. He began to wonder what school would be like next year without Rory there. He had pretty much made up his mind that he would not be going to Chilton. All that was left was to tell Luke and Lorelai. He was sure if he worded it right they would see his side. It was just easier this way, he had a routine and he would argue that he hadn't skipped in weeks now. As long as he was trying harder, they shouldn't care where he went to school. Plus, Jess was sure there was a major issue of money. He wasn't exactly sure of the family's financial standing, but he did know how much Chilton cost, and somehow he couldn't see any way that the family would be able to pay for two tuitions in the first place. Really, Jess was doing everyone a favour by not going. He only hoped his parents would see it the same way...

* * *

It was Tuesday which meant after school, Jess worked at the diner from three until six-thirty. Jess had argued with Luke at the start about the pointlessness of him ending his shift right in the middle of the dinner rush, but Luke had been adamant that those were the hours he was allowing in order to make sure the teen still had ample time for his studies and his own supper in the evening. Jess still didn't feel like it was necessary, but he'd learned to keep his mouth shut if he didn't want to lose the hours altogether.

He headed in the direction of the diner as soon as the bell rang. Luke wasn't too concerned if he got there a few minutes late considering school only got out at three, but Jess liked to get there as soon as possible in order to get a decent amount of tips in his short three and a half hour duty. On good days, if he turned his charm up, his tips could make up for the skimpy hours he got each week, which meant that he was that much closer to purchasing himself a car once he reached sixteen. It was a dream he hadn't mentioned to his parents in fear that they would not approve of the idea, so instead, he worked on the small fund wordlessly and hoped the adults wouldn't question where all his money was going.

He rounded the corner and crashed into a frazzled looking Kirk, mildly frustrated at the stall in his quickened pace.

"Jeez!"

"Oh, sorry Jess! Hey, you haven't seen a parakeet flying around the square have you?"

"No? Look I gotta get going so-"

"It's just, I'm bird-sitting this lady's parakeet for the week and it was looking a little restless so I thought I should maybe take the cage outside, so the bird could get some fresh air. Only I didn't realize that I had left the side door open when I had refilled his water container and he flew out and before I could blink he was gone!"

"Well, I'm sure you'll find him, check the trees," Jess suggested with a deep sigh, knowing full well that the bird was long gone, if not dead already. Somehow in the boy's anxious state, Jess didn't have the heart to be overly cruel towards him. On the plus, if he gave the guy a little hope perhaps he would stay out looking for the feathered animal instead of camping out in the diner like usual, holding up a table and annoying the life out of Jess.

"I hope so, let me know if you hear anyone mention seeing him, okay?"

"Sure thing," he agreed nodding once as he pushed passed the boy.

He entered the diner to see it already filled up with after school teens and a group of older ladies who Jess pinned as most likely antiquers. Not the best batch of customers to start his shift, but at least antiquers usually tipped well.

Luke approached his nephew's side when he saw him enter.

"It took you nearly ten minutes to get here, did you get kept after class?" the uncle accused out of habit.

Jess furrowed his brow, "I ran into Kirk, but thanks for the confidence in me."

"Ah not that stupid parakeet search? I mean, come on, the bird's dead right?"

"I expect to see Mrs. Martin's cat coughing out feathers next time we see it," he spoke dryly.

"Poor kid."

"Who's dumb enough to leave a living thing in the care of Kirk anyway?"

"An eighty year-old woman. Anyway listen," Luke changed the subject, "Don't bother starting because I need you to come home with me."

"What? It's Tuesday, you promised I get every Tuesday and Thursday and it's packed in here!"

"Calm down, Jess. I'll let you work tomorrow okay? Lorelai and I wanted to discuss something with you and she managed to get an hour off this afternoon. The guys are perfectly capable of holding down the fort here."

"Discuss what?" The boy huffed, curiosity outweighing his anger for a moment, but Luke simply shook his head.

"We'll talk at home, go hop in the truck, I'll be right there."

With one last long stare at the man, the teen rolled his eyes, but proceeded in the direction that was ordered. He shouldn't have really been mad, his uncle had promised him the hours the next day anyway, but somehow the idea of a discussion with his uncle and aunt didn't sit right with him. If Luke's nervous energy was anything to go by, this discussion was probably going to be one Jess would not enjoy one bit. He suddenly found himself wishing that Rory hadn't gone to the library after school to work on her history project with Lane. Two against one in any situation never ended well and he could have used the back-up.

* * *

"You don't have to look like you're headed to your execution, Bud," Luke chuckled as he pulled up to the house a few minutes later.

"Well, you won't tell me _what_ is going on, so what am I supposed to think?" Jess replied in an annoyed tone.

The man sighed, worried that his nephew was already in a bad mood, which didn't seem like the best way to start a conversation that would surly only make him more mad. He knew that they should have waited until the three were at home alone one day and not make such a big deal out of it, but Lorelai had insisted that they do it sooner rather than later. They did need to get an answer back to the school after all, and the longer they waited the harder it was going to be for them to do it at all.

He lead the way into the house and Lorelai smiled at the pair as she greeted them, cookies on the table and a soda waiting for Jess at his place. Luke noted his wife's efforts, a little buttering up never hurt anyone.

"Hey Jess, how was school?" she questioned in a chipper voice.

"Fine," he replied, looking from the woman to the man with narrowed eyes, "What's this about?"

"Look, Jess... sit down, okay?" Luke requested.

The boy obeyed, still looking expectantly at the adults.

"We wanted to talk about Chilton," Luke looked tiredly at the boy when he rolled his eyes in response, "Come on Jess, you know we have to get back to them about a decision soon-"

"Okay, I've decided not to go," the boy stated simply, shrugging with ease, "I decided a while ago that it's just not for me. I'm doing better, I'm not skipping anymore-"

"Jess, it's not just about the skipping," Luke cut in.

"Bud, we're concerned about you being fulfilled, not just about you skipping or getting good grades," Lorelai added with a frown.

"I'm fine, okay!" he huffed in annoyance.

Luke sighed long and hard before turning his attention back to the boy, "How about this, tell me exactly what it is that makes you not want to try the new school?"

"I just don't, jeez it's my life I shouldn't need to explain."

"Jess, we are responsible for you, so yes, you do need to explain because I asked you to. If there's a real reason that you don't want to go to Chilton than I want to know," Luke pressed, trying his hardest to keep the teen as well as himself calm.

He huffed, refraining from looking either adult in the eye, "I just... it's not my kind of place. I don't need six hours of homework a night and I definitely don't need a bunch of rich kids judging me all day! I'm not going to college so why waste the time in high school anyway!"

"What do you mean you're not going to college!?" Luke nearly shouted.

"Just what it sounds like," Jess spoke boldly.

"JESS."

"Okay, we'll save the college discussion for another day... Hun," Lorelai rested a hand on her husband's arm after she saw the look on his face at his nephew's words, "stay focused."

The man sighed, "We're not through with this," he pointed to the boy's chest, "You are bright enough and you shouldn't throw that away, but let's forget that for now. Jess, I'm sorry, but if this is just out of sheer laziness-"

"Babe," Lorelai gave him a look.

He met her gaze and sighed, "If you're worried about the workload then we can deal with that, but that doesn't mean you shouldn't give it a chance. We have had issues with school since you got here and if this could change things I really think we need to give it a go."

"I just don't want to," the boy shrugged again, "And in the end it's my decision."

"No, it's not just your decision. I'm sorry, but we have discussed it, and whether you like it or not we've decided that you have to at least try Chilton for one semester-"

"THAT'S NOT-"

"Jess listen! If you don't like it after one semester then-"

"I won't!"

"If you don't, then we'll reevaluate, but-"

"This is SO unfair! So basically you lied about it being my choice!"

"Hun, we didn't lie," Lorelai attempted to stop the screaming match.

"We just want to do what's best for you and sometimes you can't make that decision on your own!" Luke cute her off.

"I'm fifteen! I think I know what is best for me!"

"You're still a kid, Jess!"

"This is unbelievable," the teen fumed, "Un-fuckin-believable!"

"Hey, watch your language young man!"

"Oh sorry, I forgot I'm two, I can't be saying naughty words!"

"You need to lower your voice right now, kid," Luke warned in an equally loud tone.

"Why should I!?" The boy shook his head, fire in his eyes. Lorelai couldn't remember a single time she had seen him quite so angry and the uneasiness in the room reflected that.

"Ok, Jess, you need to calm down," Lorelai spoke softly, shooting a worried look to her husband who was red faced, "and so do you. I think we all need a cool off."

Both boys stood in silence gazing angrily at the floor and the woman sighed, "Jess, why don't you head to your room for a little bit and we'll talk some more once we're all calm."

"Like that's going to change anything," he mumbled as he turned on his heel and left the room hotly.

The woman let him go, bringing her hand to her temple and messaging before turning to her husband, "Way to just drop it on him! What happened to remaining calm?"

Luke looked up, frustration leaking from his face. He sighed long and hard, pulling out a kitchen chair and depositing himself into it, "He's just so difficult sometimes. Why can't he just accept that we know what's best for him?"

Lorelai smiled sadly, "Because he's fifteen. Did you think your parents knew anything at fifteen?"

"I know that I would have never talked to them like that," the man replied firmly, "Did you hear how disrespectful he just was?"

"He's upset, Babe. He'll come around once he has time to think. We knew this would be his reaction and he has every right to not be happy. He just has to accept that we are only doing this because we love him. I know one day, maybe not soon, but someday, he will realize that. Until then we just help him the best we can."

"Is this the right choice? I mean, maybe we are being unreasonable."

"Luke. We're doing the right thing. You know that, we've talked it through multiple times. You're only second guessing yourself because of his reaction."

"I know," he nodded sadly, "The famous Gilmore pro-con list never fails."

"Darn right!" Lorelai beamed back.

A loud crush sounded from the direction of Jess' room and Luke made a move to go check it out, but he was stopped by his wife's hand gently pressing on his chest.

"Let him be alone in there. Give him time to think. If he destroys his room, he'll clean it up later and once he's calm, I'm sure he'll be more willing to listen."

Luke nodded once, "You know for having a kid as levelheaded as Rory, you're pretty good at this."

She smiled in return, "Oh, but you're forgetting that I was not a kid as levelheaded as Rory. Believe me, I know exactly how our young man in there is feeling."

"Well it's a good thing I have you then," he smiled back.

He was worried. He was worried about Jess, about how this would effect their relationship. He didn't want him to feel as though his voice wasn't heard or that he had no control over his own life. On the same note, though, he couldn't sit and watch the boy not push himself just because he was too comfortable. Luke knew all too well what being afraid of change was like, but he also knew just how harmful it could be to avoid it all the time. Sometimes it was a necessity in life, and both Lorelai and Luke felt strongly that this was one of those times. As he heard another crash come from the other room, Luke winced. He hoped that it wouldn't take too long for Jess to see it that way too.

* * *

 **A/N- Do you think L &L are doing the right thing? Or does Jess have a reason to be upset? Thanks for all the comments on the last chapter! It's really great to hear from some new names and all you regulars too! I'd love to hear your thoughts on this one as well!**

 **(Also the overwhelming positive response to the literati relationship status in this story was really reassuring! I was really scared you guys would be mad at me for not putting them together, but I'm glad that every one of you seems to be on the same page with me about that choice!)**


	9. Chapter 9

April 20th

He stormed into his room hotly, slamming the door with a bang. Luke had no right to control his life like this! He was the one who was going to have to go to this school, not Luke, so whether the man thought it was a good idea or not was completely irrelevant.

Then practically being sent to his room like some little kid to 'cool off.' There was nothing to cool off about. They were wrong and Jess was right, there was no other way to swing it. He had been keeping his nose down and getting decent grades again, so why did they think it was okay to just uproot him like this? Just because colleges saw Chilton as a better education on paper didn't mean it was going to magically challenge Jess in ways that he had never been challenged before. School was school no matter where or how fancy you dressed it up and Jess hadn't required such mundane education in a long time.

The boy paced his room full of steam, feeling the need to punch or kick something. He hadn't gotten into a fight in a while now, but his old instincts were still hard to shake sometimes and he found that they sometimes crept up when he let his emotions get too out of control. Conveniently, he was stuck in his room for the time being with no unsuspecting person to unleash his frustrations upon. Knocking over the book leaning against his night stand had felt good, though, and soon more of the things around him started to litter his floor. One kick with a bit too much force, however, ended up causing the legs of his desk chair to give out from underneath, causing a loud crash as it collided with the hardwood floor. He winced at the loud noise, pausing for a few moments with the concern that Luke would rush in to yell at him for the tantrum even he could admit he was having.

When the door didn't swing open, he sighed.

He knew they were discussing him out there like he was some animal that needed observing in order to understand it's behavioural quirks. The conversation had been a complete joke. Sitting him down, pretending like it was going to be some mature discussion between adults until Luke swoops in and delivers the punch line. The man had even bothered to look concerned by the boy's reaction at first. Though, it hadn't taken long before his trademark yelling had commenced. The bark always worse than the bite, Jess had learned early on.

He supposed he could understand the man's frustration. Luke had always cared too much, worried too much. He knew among anything else that after the way their conversation had gone, his uncle was already beating himself up over it. Jess bit back the feelings of guilt that tried to sneak their way to the surface. He was mad at his uncle and he didn't deserve the boy's sympathy. Even if he did know that Luke really thought that his decision was the best option. Even if he was painfully aware that the man was truly only doing it because he loved his nephew and wanted nothing more than for Jess to live his best life.

The man really did make it hard to stay mad at and perhaps Jess could admit that his reaction may have been a tad harsh. Not that he agreed with what his uncle and aunt were forcing upon him, but he was still learning that there were other ways of getting his displeasure across that didn't result in a screaming match or being sent to his room at fifteen.

He sat on the bed with a sigh and picked up his old, ratty, stuffed monkey. He had been gifted the stuffed companion by a nurse when he was four-years-old and had banged his eye on a railing, requiring him to need stitches just below his brow the day before kindergarten. The monkey was nothing special, matted fur worn down from too much love and surely full of germs from never being washed. He himself had never really understood his attachment to the thing, yet still, he never could convince himself to get rid of it either.

Most nights, his monkey had been his only comfort, offering him a soft body to squeeze and to catch his tears when his mom's boyfriends had gotten a bit too rough with him, or his mom had stumbled home at stupid o' clock rambling on in a drunken slur about how his existence was a mistake and everyone would be better off without him. Back then the soft smile and kind eyes of his friend were a reassurance, silently letting him know that he would be okay.

Now, however, the monkey's beady eyes bore into him in a different way. The plastic gaze silently chastising him for being so disrespectful, for disappointing his uncle so greatly. He had messed up royally and his conscience was letting him know it through the silent judgment of his once sole companion. In frustration he threw the stuffed object across the room, misjudging his swing and hurling it into a stack of books on his dresser, causing them to tumble to the floor with a loud crash. As he watched his friend hit the floor a wave of foolishness overcame him for feeling guilty, as if he still believed the object had feelings of its own.

He let out a frustrated growl and pulled his pillow over his head.

He wasn't ready to forgive his uncle necessarily, or in any way give up his battle to stay a student at Stars Hollow High School the following year. Maybe, however, he could prove that he was mature enough to have an adult conversation on the matter. The childishness and the lashing out wasn't going to help him get the results he wanted, and if he noted anything from his parents' faces, it had been exactly what they had been expecting from him.

He would try harder in round two, he decided. If anything the calmer demeanour would aid him in catching the adults off guard and hopefully helping see that he wasn't just some kid who couldn't make his own decisions about his future.

* * *

Luke and Lorelai had let Jess stew for a good hour as they themselves worked on the best way to handle their follow-up talk with the boy.

"You need to remember to listen to him, Luke, even if you don't agree with what he's saying. It's only going to make him more frustrated if he feels like he's not being heard."

"I know... I know. It's just... it was so much easier to have these conversations with him when he was younger. He listened to me back then."

Lorelai let out a snort, "Is this the same kid who you used to call me in near tears over because of the nightly screaming matches the two of you had over homework? It wasn't easier, Babe, just different."

"Maybe. But, again, I question if we're making the right decision here. Does he really like Stars Hollow High that much?"

"I don't think it's so much about liking his current school. I think he's more afraid of the unknown. As much as he talks about hating the other kids, or being bored with the schoolwork, he has friends there, and he knows what's expected of him."

"He'll still have Rory," Luke pointed out.

"Yes he will, but he will always have Rory, no matter what. What's going to happen to Pete once he changes schools, will there still be time to see each other? Will he still have any free time at all with the amount of work this new school is going to dump on him?"

"What are you saying? I thought you were the one who thought this school was the right choice?"

"I do, Hun. I'm just trying to give you an idea of some of the concerns Jess might have swimming in that big brain of his."

Luke sighed, "I guess he had a right to feel a bit panicked when I dump our decision on him like that."

"Sometimes the smarter the kid, the more their brains like to throw five thousand worse-case scenarios at them with every decision they try to make."

Luke nodded thoughtfully, "I can help him work through those concerns though."

"Yes you can," Lorelai urged, "I have complete faith that if you guys spend more time listening and less time yelling, this situation will work out."

"Do you mind if I go in there alone? He loves you Lorelai, but I find he has an easier time talking when it's just the two of us."

"Don't worry about me, I love that kid like crazy and I know the feelings are mutual," she smiled, "Sometimes a kid just needs his uncle, just like a daughter needs her mom."

Luke affirmed with a nod, "Speaking of daughter, Rory is going to be home soon, I better get this over with."

Lorelai agreed, "Remember, less yelling, more listening."

* * *

He heard two raps on the door and let out a breath as he set his book down beside him, "Come in."

"Hey, Bud."

He knew it was Luke, he had hoped it would be Luke. Even being as old as he was, he still craved his uncle's attention after they had any sort of fight. He couldn't stand the feeling that there was still any bad air between the two of them, and though he was still partially angry with the man, he was ready to get the disagreement sorted out so that the guilty feeling that had settled in the pit of his stomach could finally subside.

"Hey."

"Whatcha reading?"

Jess flipped the book over to reveal the cover to his uncle, the man studying it seriously.

"Hmm, I don't think I've ever read that one," he admitted, causing the boy to involuntarily smirk. Small talk was never something that Luke had ever been particularly good at. Jess either, really, though books and music were usually his go to if his conversation companion was well educated in those departments. Luke tried to be and that was enough for Jess to appreciate the effort.

"So..." the man continued, pulling up the now righted chair and placing it in front of his nephew. "You know we are too alike for our own good sometimes."

"A bit."

"Look Jess, I didn't mean to drop that on you back there. It wasn't exactly how I pictured the conversation going."

He shrugged in return, suddenly finding it hard to admit to his own wrongdoings.

"And I did intend for you to have a say... or at least, you know... have you understand things a bit better, discuss your concerns."

Jess didn't know if he should roll his eyes or laugh, but he refrained from doing either for Luke's benefit. It was always so obvious when his uncle had been coached by Lorelai. The man tried, but words were not always his strong point and he didn't hold it against the man, though it was amusing sometimes.

"Well, there's not much point 'discussing my concerns' since I'm going either way, right?" Jess pointed out, not unkindly, but more as a matter of fact.

The uncle watched his nephew for a moment, "I was more hoping that we could work through the concerns together, Bud. I want you to give Chilton a try, but I don't want you going into it with a head full of worry."

"I'm not worried," Jess scowled, hating to sound so weak.

Luke held back his smile, "So you aren't worried about leaving your friends behind? You're not worried about the workload, or losing your free time? I find that hard to believe considering you mentioned at least one of those things out in the kitchen."

"I just... I don't think it's going to change anything, and if it's not going to change anything what's the point of changing everything else?"

Once again, Luke felt amazed by his nephew's words. He swore the boy got half of what he said out of a poetry book or something. If it was a different conversation he might have made a joke about it, but now wasn't the time for that. Instead, Luke just nodded.

"I understand that. I do Jess, but I also want you to understand that you don't know that it won't change anything until you give it a try. I'm not asking you to sign your whole high school career away to this school, I'm asking you for one semester. Five months and if you hate it, then I'll walk right back into Stars Hollow High and transfer you back. Does that really sound so bad?"

Jess remained silent, studying his sock foot and digesting his uncle's words. He sighed.

"You can't be on me 24/7 about getting my homework done or taking my schoolwork seriously."

"Well, you'll need to give it a fair shot, Bud, and that means putting in a good amount of effort. However, I know that school is not your number one priority, and I understand that you can't be living and breathing school day in and day out."

Jess nodded, "And I get to keep my shifts at the diner."

"I was never planning on taking those away from you. You know I don't do that unless you're in trouble or _you_ feel that you need the extra time. You're making up for today's missed shift tomorrow, aren't you?" The man reminded.

Jess nodded absently at the rhetorical question.

"Fine."

"Fine?" Luke repeated.

Jess met his uncle's eyes and sighed, "Fine, I'll do it. I'll try it." He resigned to the fact that he had given into the idea long before his uncle had entered the room.

"You'll do it? And you're not going to give me any grief about this?"

"Well, I'm probably going to give you some grief," the boy admitted honestly.

Luke chuckled, "I guess I can only expect so much from you, but thank you for hearing me out. I'm proud of you for giving this a shot, and I meant what I said. After five months, if you feel no difference, then you can transfer back."

The teen nodded once, "Thanks."

Luke patted the boy's knee once as he stood, making to leave the room when the teen spoke up once more.

"You know, I agreed to the school thing, but taking the bus every day is going to suck. Don't you think Rory and I will need some wheels?" He asked raising his eyebrows and causing the man to laugh.

"You stick it out the five months and decide to stay, we'll talk once you actually pass your driving test."

"You know I'll pass!"

"Yeah, well you're going to have to get used to the bus for a while," the man smiled, "But nice try."

Jess shrugged, "I figured it was as good a time as any."

* * *

April 26th

"Why are we here again?" Jess asked as the family stood at the front door of the Gilmore mansion.

"Because it's my birthday and my parents wanted to see me," Lorelai responded, not breaking eye contact from the huge door.

"And since when has that mattered before? You didn't even invite them to the wedding," Jess furrowed his brow.

"Yeah Mom, didn't you say after the last time that we were never going to set foot in this house again?"

"Guys, give Lorelai a breather here," Luke spoke up, noticing his wife already going into panic mode and knowing she didn't need the kids breathing down her neck as well.

"I'm getting older, and when you get older you realize that holding on to grudges gets you nowhere," she stated.

"Seriously Mom?"

"Yeah, you're like the queen of grudges!"

"Alright, let's just get this over with, okay?" Luke spoke up, "Best behaviours everyone," he reminded as he finally knocked on the door.

"I don't think it's us you have to be telling that to," Jess muttered, remembering his last disastrous encounter with the Gilmore elders as the door swung open and a nervous looking maid gazed back at them, "Yes?"

"Salingers, party of... well four."

"Not your best bit, Mom."

"Yeah well, didn't think that one out."

The maid stared at the dumbly, "Salingers?"

"Urgh uh, no, Gilmore, Lorelai, the daughter?"

"Oh yes, right this way Mrs. Gilmore."

"Well Gilmore-Danes now, Mrs. Gilmore is my-"

"Lorelai."

"Mother. Uh, hey Mom, long time no-"

"Yes well, when we weren't invited to your wedding we got the message loud and clear. Rory, I hope you got the birthday and Christmas presents we sent you."

"Oh... yes grandma, I sent you thank you cards, did you get them?" Rory spoke up nervously, remembering the interesting gifts that the girls had swiftly exchanged at the mall each year.

"I did. Of course, we weren't sure who exactly it was sending them. You know without a phone call it's really hard to tell."

"Lorelai, long time no see," Richard greeted, entering the room.

"Hi Dad."

"And this can't be little Rory? She's tall!"

"Of course she's tall, she's a Gilmore. She's practically towering over this boy."

"Jess, Mom. His name is Jess."

"Well you know what they say, girls always grow faster than boys," Luke spoke up awkwardly, cutting through the mother/daughter staring contest.

Emily turned to Luke with a smile that made him uneasy, "Hello Luke, you've been well I presume?"

"Never better actually."

"How's that diner of yours, Luke?" Richard asked conversationally. "Any plans to franchise?"

"It's doing well, but uh, no, I'm more of a single establishment kind of person."

"Hm," Richard's gaze bore into him and the younger man shifted uncomfortably.

"Well, come into the living room for drinks," Emily ushered, suddenly impatient, "No use standing at the door like solicitors."

Rory and Jess glanced at each other through the tension. Neither one of them could quite figure out how the family had ended up back at the Gilmore mansion, but whatever it was must have been important because this visit was not promising to be any better than the last.

"Jess, Rory, could you give us a few minutes? Maybe go hang out upstairs," Lorelai requested as the group shifted towards the other room.

Both teens looked at her with confusion written all over their faces, silently asking what was going on, but both of them knew better than to voice any sort of concern in front of the elder Gilmores.

"Ok Mom, c'mon Jess," the girl pulled the older boy along even though he didn't look quite as eager to leave the room.

"What was that about?" Jess whispered once they were out of earshot.

"No clue."

"Rory, wait, should we not... I don't know, listen or something?"

"Mom asked us not too. I don't know about you, but I think she'd be pretty upset if she found out we did, and I know Luke would be too. If they trust us, they will tell us later."

Jess shook his head as he continued walking once more, "We're fifteen. Aren't we a little old to be asked to leave the room so the 'adults' can talk? I don't know Ror, something about this whole night just doesn't sit right with me."

"You think it feels right to me?" Rory asked as she steered the two into her mom's old room, "Something's definitely up, but I'm not really sure what you think we can do about it."

"I don't know. I just think we deserve to know what's going on."

* * *

"Lorelai, what is going on?"

"What is the meaning of this Lorelai?"

"Mom, Dad, could you just sit down, Luke and I have something, I mean it's actually good news-"

"Oh my God are you pregnant?"

"Mom! No! Not that it wouldn't be totally fine if I was, I am married and thirty-one after all."

"Yes, married, so we've been told."

"Look, whatever crap we've been through in the past, that's in the past now. This is good, but we need your help. Rory and Jess got into Chilton."

"Rory got into Chilton! That's wonderful!"

"I always knew she was a smart girl," Richard concurred.

"Yes, Rory _and Jess_ got into Chilton, actually Jess had his position personally reserved because his grades were so exceptional."

"I can't imagine he could have done much better than Rory. It would take a lot of brains for anyone to beat her smarts," Richard scoffed.

"Well imagine it because he did Dad, and that's great! Rory's more than happy for him and she got in too. They're both smart, insanely smart."

"Well, I'm sure you didn't come all this way just to have dinner with us and tell us how much smarter some random boy is than our granddaughter," Emily spoke, upset.

"He's not some random boy Mom! He's my stepson!"

"Step-nephew more like."

"Stepson, step-nephew, same difference! Luke adopted him and Luke and I are married so he's my kid too and I would appreciate it if you started treating him that way!"

Emily rolled her eyes and crossed her arms.

"Lorelai, why are you here?" Richard got back to the point.

"It's my birthday. I'm sorry that I thought my parents would want to celebrate with me."

"If you would ever come near us maybe we wouldn't be so shocked," Emily spoke up.

Lorelai sighed, going in circles was her parents forte.

"Come on Lorelai, why are you here?" Richard pressed again.

She exhaled long, looking to Luke who looked every bit as uncomfortable as she was. He opened his mouth to help her out, but she quickly shook her head and answered her father. "Rory and Jess got into Chilton."

"Yes, we've established that" Richard nodded, "And..."

"And Chilton's, well... expensive."

"So, you need money," the older man finally established.

"We have some, in savings and Luke's dad left us a very generous bit, but-"

"But, you need money."

Lorelai didn't expect it to feel this degrading asking her parents for the money. She knew it would be bad, the worst thing she's ever had to do even, but this was even worse than anything she could have imagined.

"Obviously you think we don't deserve it. We didn't invite you to the wedding and we haven't talked to you in a while, but please think about it as for your granddaughter and, well technically grandson, even if you don't want to think of him that way. This isn't for me, or Luke, this is for Rory and Jess."

There was a long pause before Richard looked at her with a smile, "I'll get the chequebook."

Lorelai smiled wide and Luke was just about to open his mouth to thank the man profusely, but their happiness was cut off quickly by the sound of Lorelai's mother cutting through the room.

"Not so fast Richard."

Even Richard seemed shocked by his wife's words, speaking up instantly, "Emily it's Rory."

"I know, and I absolutely agree we want to help our granddaughter in any way we can, and even the boy if only because Rory was so defensive of her friend the last time she was here, but I have a request first."

Lorelai groaned, knowing full well that Emily had her right where she wanted her and not at all shocked by the woman milking the situation.

"I want a weekly dinner. A meal with you and Rory, once a week."

Lorelai sighed hard, giving her husband a look, but he only shrugged, as if he thought it was getting off pretty easy.

"Mom..."

"Now Lorelai, I think this is a very reasonable request, especially considering we will be a big part of Rory's academic life now. We want to see how our money is benefiting her!"

"Mom, stop, I was only going to say that Luke and Jess are a part of our family now too, and if you want a meal with me and Rory, you will have to have all of us. All or none Mom."

The woman stared her done, long and hard, "Fine." She finally agreed, "We will give you the money and you will give us Friday night dinners."

"Friday?"

"I think Friday works out best for everyone. There's no school the next day so the kids won't have to worry about homework or getting up early, and I have no DAR functions that night," she explained.

Another sigh and an encouraging nod from Luke's direction made her give in, "Fine. Friday night dinners it is."

"Wonderful!"

"I'll get the chequebook."

* * *

 **A/N- Honestly I didn't want to add in Friday night dinners because I don't particularly like writing Emily and Richard, but I felt like I sort of had to. We'll see how much I can get around adding them to the chapters haha. Anyway enjoy! And leave a review if you can, no matter how short or long I love to hear them!**

 **(Also I wrote my first This Is Us one-shot! It's called Brothers and Fathers. If you watch the show and want to check it out and/or leave a review I would appreciate it!)**


	10. Chapter 10

April 28th

"Jess where were you? Rory said she couldn't find you after last period. If you're skipping school again, I swear-"

"I'm not, relax," Jess cut his uncle off abruptly as he walked into the house, "I just had some things to take care of after school and I didn't have time to wait for Rory to tell her."

"What sort of 'things' could have possibly been so important that you couldn't spare a minute to let someone know you wouldn't be home until after seven? Come on Jess, we were worried."

"It's not important, I'm sorry I worried you, I'll let you know next time, okay?" He promised, attempting to push past his uncle towards his room, but Luke was making it difficult. Eventually he succeeded, although his uncle was hot on his tail.

"Oh no Bud, that's not going to fly," the man informed shaking his head, "I want to know where you were tonight and neither of us are leaving this room until you tell me."

Jess sighed, rolling his eyes to the ceiling before licking his lips and returning his gaze to his uncle, "I went to a job interview."

"A job interview?" Luke brought his hand up to his ear as if he was hearing wrong, "Gee, I didn't know the diner was so terrible that you're seeking other employment. You're messing with me right?"

"Well, actually, first I had a meeting with the guidance counsellor to see about a scholarship, but apparently the Gilmore's have already sent in the first cheque and Chilton now thinks we have the money. They said they need to save the scholarships for kids who actually need it," Jess rolled his eyes.

" _You_ had a meeting with your guidance counsellor?"

"Is that really the part you're stuck on with that whole speech!? Yes _me_ , and I hope you're happy that it was all for nothing since you didn't think to talk to us about the money issue before the Gilmores."

Luke sighed, "Jess we have talked this subject to death, it's not that big a deal."

It hadn't taken the kids too long to knock it out of the parents exactly why they were made to leave the room at the Gilmore mansion, and as soon as they found out what their parents had done they had both been quite vocal about their displeasure.

"It is a big deal, which is why I went to McDonald's straight after my meeting."

"McDonald's?" Luke asked baffled.

"McDonald's hires fifteen-year-olds and since I can't get a scholarship I want to be able to contribute something more than the few hours I'm getting at the diner. I could work there on the nights I'm not at the diner, plus weekends."

Luke shook his head,"You're going to call them right now and tell them you're quitting."

"They haven't even hired me yet! And why should I?"

"You shouldn't be worrying about paying for your high school education Jess. There's a reason I give you the hours I do at the diner. You don't need to be working any more than that at your age. You know that's part of our deal. When do you plan on doing your schoolwork with those hours? Huh?"

"It's a better option than relying on the Gilmores," Jess huffed, averting his eyes as the conversation was obviously not going his way.

Luke closed his eyes and sighed, "Please trust that we are doing what's best, Bud. I know you don't like the arrangement we made, I know it's not ideal, but we will survive and your education is worth it. So will you please go back to putting your money towards more important thing? Like maybe that car you've been saving for," the uncle gave his nephew a knowing look and Jess' eyes flicked up.

"How did you-"

"Jess you're my kid, don't you think I know how your mind works?"

"I thought you would want me to save it for more important things," the boy admitted.

Luke only shrugged in return, "Well I do think you should be putting some of it aside for your future, but I don't see the harm in working towards a car too. Like you said, if you don't want to take the bus you're going to need one sooner than later."

Jess smiled with a slight nod.

"You're going to call McDonald's tomorrow and tell them you don't need the job anymore, okay?"

Jess sighed, knowing it was a lost cause, "Fine."

Luke nodded once, giving the boy a small small, "In a month when you're out of school we'll talk about giving you extra hours for the summer, sound fair?"

"Okay," Jess agreed. The extra hours would be a nice advance toward the car, "That would be good."

"Now it's nearly eight and I'm going to guess you haven't even started your homework yet, right?"

Jess rolled his eyes, "And just when I thought we were having a nice moment!"

Luke barked out a laugh as he turned to leave, "Get it done, nephew!"

* * *

April 29th

"You and Dean were awfully cozy today," Jess noted to his sister as they walked home from school. The siblings and Lane had been allowing Dean into their group at lunches the past few days and though Jess was trying for his sister, he still didn't exactly have the warm and fuzzies for the guy, especially when he and Lane had to sit and watch as the blossoming couple got a bit too mushy whenever they were together.

"We're just friends, Jess," Rory rolled her eyes as she did every time Jess brought up the subject.

"Huh, Lane and I sure don't giggle at each other as we converse, and yes you just made me use the word giggle, I hope you're happy."

She turned to the boy as they continued to walk, "Are you ever going to leave us be?"

"Are you ever going to admit that you like him?"

" _Jess_."

He sighed. As much as the guy bugged him, Jess knew that he would have to accept the fact that he was most likely going to be a part of his sister's life, and if he wanted to keep his relationship with Rory good, he was going to have to drop the snide remarks.

"Yes, sorry, okay? Do whatever you want with Dean and I'll keep my trap shut," he surrendered.

"And you'll try to be friends with him?"

" _Rory_ ," he mimicked her previous tone.

"He likes you, he told me."

"Oh gee, great. Maybe later we can hold hands and skip."

"Come on, Jess. Please."

Jess sighed as they reached their porch, "Fine, I will attempt to get along, I do let him sit with us at lunch if you haven't noticed."

"Yeah, and he's noticed your dagger eyes at him too."

He shrugged his head to the side, "Ok maybe I haven't been as subtle as I thought."

"You think!?"

They reached their yard as the door swung open forcibly.

"Heeeello children!" Lorelai sing-songed, stepping aside with a wide grin to allow the pair through the door.

"You're happy," Jess noted, grabbing an apple from the counter as Rory set her books down on her bed.

"I just got off the phone with my mother."

"I've never seen you this happy after getting off the phone with Grandma, Mom," Rory gave her a bewildered look, joining Jess at the table to start on her homework.

"Please tell me you guys had a big fight and she's refusing to give us any more money and therefore we get to can the whole 'Friday night dinner' deal before it begins?" Jess asked hopefully, already dreading the next night.

"Why would that make her happy?" Rory asked.

"It would make me happy," Jess answered with a shrug, biting into his apple.

"No, that is not what happened, but you're not too far off kid," Lorelai praised, bumping Jess' shoulder, "I did get us out of them for the time being!"

"How did you do that?" Rory questioned in disbelief, knowing how strong-willed her grandmother was.

"I simply called her and we talked," Lorelai shrugged.

"Mom."

"Okay, maybe not talked, yelled a bit, bickered, threatened. Then, I told her that the school had offered us a scholarship and maybe we didn't need her money after all."

"Mom! Way to lie!"

"I prefer little fib, dear daughter. It was for the greater good!"

"I'm guessing she didn't take that very well," Jess concluded.

"I explained to her that we weren't actually going to be using the money right away and she agreed that we didn't need to start the dinners until September... after she yelled a bit more, but that's beside the point," Lorelai waved her hand, "She didn't want to miss out on roping us into her deal, so she compromised. Well as much as my mother can compromise..."

"So were seriously out of it?" Jess smiled.

"For four months," Rory corrected.

"I'll take it for now," Jess sighed, his apple suddenly tasting better than it had a moment before.

"Amen," Lorelai agreed, "Now I say we wait for my lovely hubbie to come home and then go out to celebrate!"

"You know, that was pretty sneaky of you, Mom. If you don't watch out I would say you're starting to become a little bit like an older Gilmore girl we both know," Rory teased playfully.

"If you are trying to tell me I am like my mother you can forget the double scoop of ice-cream later tonight Missy!"

"Who said you were anything like your mother!?" Jess feigned shock, "If anything I'd say you're the furthest possible thing from her!"

"Ahh see that's the words of a boy who's going to get three scoops! Take notes Rory!"

Jess stuck his tongue out at Rory and she playfully smacked him as she shook her head, "Brown-noser!"

"Only if I get chocolate ice-cream and I miss my mouth."

* * *

"Why aren't bowling shoes in fashion outside the bowling ally, I'd wear them!"

After ordering everything off the menu at Al's Pancake World, even the pancakes surprisingly, which may have been a mistake, the small group, bellies too full, continued their celebration and found themselves at Stars Hollow's oldest (and only) bowling ally. The girls thought it would be a laugh, Luke had agreed if not only to give everyone a bit of exercise after the insane amount of food they had just put into their systems, and Jess only hoped that nobody from school would see them at quite possibly the lamest place in town.

"They are literally the most uncomfortable shoes on the planet," Jess grimaced at his step-aunt as he tied his rentals.

"Probably the leading caus of the world's foot fungus problem too," Luke agreed.

"Yes, but they're cute! Right Rory?"

"Sure, in a sign me up and put me in a league sort of way, all we need are some matching jerseys."

"Please, don't give her any ideas," Jess begged, standing up straight.

"Alright, what names do you all want to call yourselves for the score screen?" Lorelai questioned, filling out the card for the waiting attendant.

"How about 'Jess'," the boy rolled his eyes.

"Nooo, you have to have something cutesy! For example, I'll be... Pink Flamigo! Rory?"

"Ooh! I'll be Jean Louise!"

"As in Scout from 'To Kill A Mockingbird'?" Jess smirked at her.

"Maybe..." Rory shrugged, "I've been doing another read through!" she defended.

"Ok, Luke?" Lorelai moved on.

"Just Luke is fine," he sighed, knowing he was wasting his breath.

"Honestly, like uncle, like nephew," she shook her head, "Fine, DinerBoy1 and DinerBoy2. There," she sighed putting her pen down and handing the sheet to the person at the counter to put on the screen.

"You're up DinerBoy1," Lorelai announced, smacking his butt as he grumbled past her, causing him to go pink in the face.

"Hey doesn't that girl go to our school?"Rory questioned to Jess as Luke took his turn. Jess turned to see a girl with short bleach blonde hair accompanied by a few older boys that most certainly did not go to their school.

"Probably," Jess shrugged, "Great, we have a witness now."

"I sure hope those are her brothers," Lorelai commented with a concerned look that could only be reached by a mother, "She's too young to be hanging around with boys... men that old."

"Shane! You're up," Another girl called from their lane.

"Ugh," Rory groaned.

"What?" Jess rose his eyebrow.

"That's Lindsay Lister. She hangs out with Dean sometimes."

He looked over at a slightly taller, slightly longer haired blonde approaching the other and saw the envy in his sister's eyes.

"Jealous are we?" Jess smirked.

"No!" She smacked him in the stomach, "I just don't really like her, that's all."

"Hey, no hitting," Lorelai spoke half-heartedly as she came back from her turn, "I thought we were past the toddler stages."

"Dean's not here, so relax," Jess commented just to his sister, "It's your turn."

"It wouldn't matter if he was," Rory feigned indifference as she got up.

"Sure it wouldn't," Jess mumbled to himself as she walked away. He would definitely be teaching Dean a lesson if he hurt his sister that was for sure.

In the end the family had discovered that none of them were set to be bowling all-stars and the jokes about the jerseys had definitely been nixed. With only Luke reaching a score of over one hundred, the four exited the ally with their 'reward for playing a sport' candy in hand.

"So much for working off our dinner," Luke commented as they walked back to their house.

"We're walking it off right now!" Lorelai countered.

"You really want to say that as you're shoving gummy worms and Milk Duds in your mouth?" The man questioned with an eye raise.

"You know Uncle Luke, it's a good thing we moved in with them, otherwise I never would have discovered my own stomach of steal," Jess pointed out.

"They've wrecked you is what they've done! You were a healthy and responsible eater until they got their hands on you, now I'm outnumbered."

"Oh I was always feeding him extra cookies when you sent him to my house," Lorelai divulged.

"Yeah Luke, you only thought he was healthy and responsible," Rory agreed, "We ruined him long ago."

"Unbelievable," Luke shook his head, though the news wasn't exactly a surprise to him, "You're all brushing and flossing your teeth when we get home! I don't care how tired you are!"

"Whatever you say Uncle Luke," Jess shrugged with a smile.

"Are you ever going to grow out of that one?"

"Maybe when you stop reacting to it," the teen threw him a cheeky grin.

He dodged the swing to his head easily and Luke only shook his head. "This family is something else."

"Oh you love us!" Lorelai teased, pulling her husband in close.

"You're alright," he shrugged back.

"I am the one that got us out of Friday night dinner tomorrow remember... more like sixteen dinners actually," Lorelai reminded, "I'd think about being nice to me or else I'll tell Mom and Dad that we're all busy, but you'd LOVE to go visit them!"

"You'd have to call your mother again to do that," Luke remarked.

His wife went from grinning to frowning, "Okay, you've got a point."

"Well I for one am happy. It would have sucked to have every Friday of summer booked," Jess spoke up.

"Yeah and there's only one month of school left," Rory agreed, "Now we don't have to worry about missing study time to go there. We'll be busy enough with exams coming up."

"Yeah because that's the first thing I would have worried about," Jess mocked sarcastically, "We're already in Chilton, Rory, and these exams might be the last ones we have to slack off a bit."

"Jess! I'm not going to slack off at the most crucial part of the year! These scores will still go toward our GPA whether we're in Chilton yet or not!"

"And you're not going to slack off either, right Jess," Luke rose his eyebrow, causing Jess to sigh exasperatedly.

"I was just messing around guys, jeez."

"Sure you were, kid."

"I was!"

"Uh huh."

"This family is impossible!"

* * *

 **A/N- I'm here I'm here! This was not supposed to take so long but between my best friend and guinea pig both getting really, really, sick, my priorities have been elsewhere. I know it's a bit short but I wanted to get something up for you guys. Also, I really want to move ahead to the Chilton stuff (which is part of the reason I needed to make the Friday night dinners not start right away) so I THINK the next chapter will jump ahead a few months!**

 **If any readers are still around let me know what you think and I promise more interesting chapters are coming!**


	11. Chapter 11

September 4th

The summer had zipped by in the blink of an eye it seemed. The first summer Jess had been allowed to work what he would consider was more like part-time than what Luke had allowed during school. He had appreciated the extra money that was slowly building in his car fund tucked safely in his sock drawer and honestly, he sort of appreciated that Luke hadn't allowed him to work full-time hours as it had made time for Jess to enjoy his summer as well. Luke always seemed to know the balance that would work best for Jess, even though Jess would never admit that to him.

Saying goodbye on their last day of Stars Hollow High hadn't been too hard for him and Rory. They knew they would still see Lane and Pete regularly and the rest of their classmates weren't much of a concern to either of the teens. The eve before their last day, Rory had been going on and on about missing a few certain teachers, but in Jess' mind, they could all stuff it. If he never had to see Ms. Harper again, it would be too soon. Mrs. Truly was sad to see her two best students go, but even Jess had agreed that the two would keep her updated on their progress and come to her with new book suggestions when they could. When the last bell rang, the siblings were officially Chilton students, and Jess only hoped he wouldn't feel the need to look back.

He couldn't believe how fast the last few months had gone. He had always heard time goes faster the longer you are living and he supposed it made sense. A four-year-old would feel as if a day crawled by as one day in their life was a huge chunk of their entire time on earth. Yet, to a forty-year-old, one day, twenty-four hours, didn't make a huge impact in the grand scheme of things. It was this summer in particular that made Jess start to realize he was getting old enough to not notice the moments ticking away before they were gone altogether.

"Here sweets, I hemmed your skirt for Monday," a frazzled Lorelai handed the plaid piece to the girl as she whirled through the room. "Jess for the fiftieth time I need you to try on your pants. Chilton made themselves very clear that you are to look sharp. I doubt that includes sending you to school with three inches of pant leg dragging on the floor."

"If you know it's three inches, then why do I have to bother trying them on?" He was being difficult he knew, yet the possibility of holding off wearing that awful uniform until the very last minute was too tempting not to try.

"It's either drag or have your ankles show kid. Those are your options if you don't want to put on the dang pants."

Jess sighed dramatically, "I don't want to hear a single word about how I look like a cute little boarding school boy," he warned snatching the garment from her clutches.

"Oh come on, they _are_ cute!" She defended as he shut the door.

"We need to get him a date, he's far too grumpy," Lorelai concluded turning to her daughter. "Speaking of dates, are you still going out with Dean tonight?"

Rory rolled her eyes, "It's not a date, Lane's going to be there. Besides, I'm pretty sure if anything was going to happen between us, it would have by now," her expression changed to glum.

The mother gave her daughter a sad smile, "Don't fret too much over it sweets. You're young, maybe he's scared to make the first move."

"Are you saying I should make the first move?" the girl asked wide-eyed. "Because I'm pretty sure that's not an option."

Lorelai laughed, "I'm pretty sure it is an option if you want it to be. But just give him time Hun. If I've learned anything about relationships it's that they always take lots and lots of time," she rolled her eyes playfully.

The teen sighed with frustration, "Fine. I'm not a patient person you know."

The woman laughed out loud, "Well you are my daughter."

Jess chose that moment to push open his door, "They're like a foot too long!" he grumbled, dragging the long fabric along with him.

"Ah, and why Lorelai are you making me try these pants on again?" Lorelai replied in mocking.

"Yeah, yeah," Jess waved his hand, "Can you just pin them so I can take them off?"

"Somebody's crabby for a Saturday," the woman noted as she got to work.

"The last Saturday before school starts does that to me," he concluded.

"Well, I for one am glad school's starting. You have been bored since the start of August."

"When have I ever complained I was bored?" Jess countered in defence.

"You didn't have to complain. I know you kid. You've been driving me up the wall," Lorelai pointed out, "Your big brain needs to be challenged."

"Yeah and we all know school does that," Jess added sarcastically, rolling his eyes.

"Yes," she nodded, "This school will. I know you have doubts, but I'm confident you're going to be much happier there."

Jess gave a doubtful look as Rory spoke up, "I know I will! Did you see their library Jess!? I might not even make any new friends. I'll just spend all my free time in there," She joked.

"Gee that's healthy," Jess teased, though he imagined himself doing just that. He still wasn't quite convinced the kids at their new school would be any better than the ones at their old. Probably worse considering they were all coming from a background like the elder Gilmores. He would have to take up smoking just to cope, no matter what Luke would say. Okay maybe not.

* * *

September 7th

"Alright, just one more picture!"

"Lorelai," Jess sighed as he and Rory stood on the front porch dressed in their newest threads and sporting brand new backpacks sitting neatly on both shoulders. Like a couple of preppy kids, Jess thought absently.

"Yeah Lorelai I think they've had enough," Luke stepped in. They had been taking photos for the last ten minutes after all.

"Oh okay," she relented, resting her camera loosely on her hip, "You know you'll be glad to have these pictures one day."

"Mom, we do appreciate it!" The prodigal daughter assured, "But you'll see us in these uniforms every day for the next three years. There will be plenty more photo opportunities."

"Better not be," Jess mumbled as Lorelai exclaimed, "But not 'first day at Chilton' photo opportunities! Luke, can you believe how big our babies are? The next thing you know we'll be taking photos of them moving into a college dorm!"

Luke nodded once, allowing himself to smile proudly at his kids as well. The truth was, they were growing up fast. He realized it more and more each day. In another few months Jess would be driving and it would only be a blink before they were moving out of the house. These thoughts made Luke start to feel panic creeping up through his body, though, so instead, he ushered them along. "They won't be going to college if they don't make it to their first day of Chilton first, and your bus will be here in less than ten minutes, so get a move on."

"If we miss it we'll just catch the next one."

" _Jess."_

"I'm _kidding_."

* * *

The bus dropped the kids off right in front of the school and for a moment the pair stood in awe at the grand architecture.

"I don't think I'll ever get used to the size of this place," Rory admitted, staring at the large building.

"Maybe by graduation," Jess hoped, suddenly feeling slightly uneasy as well. "You ready?"

"As I'll ever be," Rory took a deep breath.

They picked up their schedules in the main foyer with the rest of the students. It was slightly less awkward to be the new kids on the first day of the year since everyone was learning a new schedule as well and for that the siblings were grateful.

Jess found their schedules side by side and grabbed them off the table just as a familiar face stormed into his personal space.

" _Move,"_ Ordered the irritated voice of a blonde girl Jess recognized from their tour the previous spring. Glaring girl, he recalled.

"Well aren't we bright-eyed and bushy-tailed this morning," he drawled to her sarcastically.

"I'd be a little more 'bushy tailed' if I didn't have all these incompetent new kids fumbling around like chickens with their heads cut off," she snapped back as she grabbed her schedule off the table.

"What's your problem," Rory spoke up with a face.

Her gaze focused on them once more and she began sizing them up with a cold look. "You're my problem," she informed, staring Rory down. "You and your boyfriend thinking you can just waltz in here and upset the whole dynamic of this school."

"He's my brother," Rory corrected with irritation.

"Yeah and right now he's getting on my last nerve."

"He's just standing there."

"Exactly. Listen, I own this school and I don't care how many recommendations from your English teacher you have or how high your test scores are, this is my turf and you'd do well to remember that."

The girl pushed passed Jess, storming down the hall as students tripped to get out of her way.

Jess shook his head, "What a freak."

"She's definitely intense," Rory noted.

"That's Paris Geller," a nervous looking blond informed the pair, "You'd be best to stay clear of her unless you want your life ruined."

"That's a bit dramatic, don't you think?" Jess eyed the jumpy lad.

"If you pose a threat to Paris Geller, she makes you sorry for ever auditioning for that Broadway play, believe me," he informed with horror in his eyes, "She doesn't even like Broadway," he mumbled to himself as he took off down the hallway, books pulled tightly to his chest.

"Did we just walk into 'The Breakfast Club'?" Jess asked shaking his head.

"It's all very peculiar," Rory replied thoughtfully as she watched him go, "What's your first class?"

"English, Mr. Medina."

"Me too," She smiled, glad that they didn't have to part ways just yet.

* * *

They found their first class without much difficulty, unfortunately realizing that they shared first period with none other than the Chilton Queen herself.

"How many classes do you think we have with her?" Jess whispered as they searched the room for two empty seats. Jess usually liked to sit in the back of the class whereas Rory preferred the front. Promising not to abandon each other on the first day unless absolutely necessary, they compromised on desks closer to the middle of the room. Rory turning down Jess' plea for seats by the window, if only because she knew it would distract her brother and that was the last thing he needed.

"Hopefully just one, otherwise it's going to be an interesting year," Rory sighed back.

As they settled into their seats, Rory watched as a medium-sized blond boy entered the room and sized her up right away. She heard him whisper to his friend, "Who's that?"

"New kids I guess?" The other boy shrugged and Rory turned away, feeling like an animal at the zoo.

"Just ignore them Tristan, they're of no interest to you," Paris spoke up from two desks over.

Tristan, as they just learned his name, only smirked and moved closer, "I think they're very interesting," he spoke, though only looking at Rory, "Tristan Dugray," he held out his hand, "Looks like we got ourselves a Mary."

"Oh, my name's Rory," she corrected.

"Whatever you say, Mary," he only smiled back and Rory was left without words.

"She said her name's Rory," Jess spoke up for her, clearly agitated by the whole production.

"And who do we have here?" Tristan sized him up, "I think I remember hearing about you. You're the one with the chart-topping test scores aren't you? A personal invitation to Chilton," the blond recalled to whoever was listening. "Well Prep, you must be yearning to get some learning started. I hope we're not all too dumb for you."

"Jeez if I didn't know any better I'd say the zip code of this school was 90210 with the way you all act," Jess shook his head.

"Into girly shows too I see," Tristan smirked.

"Just calling it like I see it," Jess shrugged with ease.

A middle age man chose that moment to enter the classroom and called everyone to attention, "Find your seats quickly please, we have a lot to go over today."

The boys gave each other one last look before Tristan pushed off the desk he was leaning on and found his seat. Jess shook his head to Rory who only shrugged in return as she focused her attention on the man who was now standing at the front of the room.

It was then that Jess first got a look at their new Lit teacher. He was middle-aged, yet that didn't seem to stop nearly every girl in the room from staring with stars in their eyes. Though he knew she hated it when he distracted her in class, he couldn't help but whisper to his sister.

"Please tell me you're not going to go all doe-eyed with this guy too," he gestured to the room of smitten gals.

Rory however, only made a face. "Not factoring in the age difference, he's more of my mom's type than mine anyhow."

"So he's Luke level hot?" Jess made a face and shot another glance at the man.

"I told you, it's too gross to think about."

"I'm sorry I asked," Jess agreed, turning back to the front of the class and realizing he had better start figuring out what the man was talking about if he wanted to try to keep up with this new school.

The class was long and there was definitely no ease in, 'let's get to know each other' period. Jess wasn't put off by this. He actually found the class sort of interesting and had to admit that the guy was more than just a pretty face, he really did seem to know what he was talking about too. He talked easily with the class and let the discussion come naturally, something Jess respected. Jess almost felt the urge to raise his hand and join in at one point, but he didn't. He wasn't quite there yet.

English classes were never all that bad, however, and it didn't ease the way for the rest of the day. By lunchtime, Jess already had an arm full of textbooks from the first half of his classes. Homework was going to drown him by eighth period he was sure of it. He was already exhausted. His fear that the new school would be hard work was an understatement and so far the classes weren't persuading the teen either way. In some ways, he could feel they were more challenging, but mostly they were the same old classes with double the amount of work involved. Already the thought of sitting at his desk all night pouring over his work sounded tiring and drained his spirits.

"Jess!" Rory called, grinning wide when she saw her brother passing by as she exited her classroom.

"How was Psych?" the brother asked once they were side by side.

"Great! You know I could deal with fewer choice students, but these classes are amazing! I already feel like I've learned so much and it's only day one! How was Chem?"

"Not as fascinating as Psych evidently," he smirked.

"Oh come on, admit it, you don't hate this place like you thought you would."

"I'll admit that we're never going to see the light of day again with all this work they're forcing on us. I'm serious Ror, there's got to be some child labour law against it."

The girl only shrugged, "Maybe it's a bit excessive, but it's worth it if it's going to get us into better colleges, right?"

The boy rolled his eyes, not prepared to start yet another argument about whether or not Jess would even be attending a post-secondary school in three years. "You hungry? I'm starved and if we don't hurry we'll miss all the good escargot in the cafeteria."

He turned quickly in the direction of his locker, pulling Rory to follow suit only to slam into a familiar elbow forcefully.

"Oops! Might want to watch where you're going, Prep," Tristan spoke as the shorter boy's books tumbled to the floor.

"You got a problem man? Caus I can make you mine," Jess threatened, slamming into the blond's chest. He had learned how to handle a bully years ago and cocky dicks never troubled him anymore.

"What is going on here?" Jess watched the principal march towards him.

Tristan straightened up immediately, "Sorry Principal Charleston. I accidentally ran into the new kid here and I guess he got the wrong idea about my actions."

Jess opened his mouth to defend himself, but the man beat him to it.

"We do not condone violence of any kind at our school Mr. Mariano. I advise you to adhere to that. This is your one and only warning on the matter."

Jess saw Tristan's smirk from the corner of his eye as he apologized and attempted to look contrite. He would get that asshole back that was for sure.

Once the principal was out of earshot the blond spoke up. "Might want to leave the bad boy act at home Prep. You don't pull it off well."

Jess attempted another move toward him, but Rory pulled him back, "Jess, he's not worth it."

"Listen to your girlfriend, wouldn't want a Prep like you to get detention now would we?"

"He's not my- Ugh never mind! Let's go Jess!"

"See ya Mary"

"It's Rory!"

* * *

"How was your day?" Luke asked the teens as they returned home.

"Crap," Jess grumbled, throwing his book bag on the couch and stomping to his room, swinging the door closed behind him.

"Rory?" the man looked expectantly, "Care to fill me in?"

"It could have gone better," she shrugged but smiled a moment later. "The classes were great!"

"Yeah? You sure have quite the armload of books. That all homework?"

"Chilton doesn't mess around," the girl's smile widened. The only kid in history to love schoolwork that much, Luke shook his head.

A silence rested between them as they stared at each other, Rory eager to put her books down and get to work. Finally, Luke spoke his mind, asking the question he knew Rory had the answer to.

"Should I go talk to him," Luke motioned in the direction of the disgruntled teen.

"He'll be okay," she assured, "You know Jess has a hard time with change. He'll be settled in a few days."

Luke nodded. If there was one thing he knew Jess didn't handle well, it was change. It wasn't an obvious character trait and on the outside the boy usually appeared calm, cool and collected in any situation. But, after taking care of his nephew for as long as he had, he was more than in tune with the signs. The nervous habits; blasting too loud music when he wasn't accustomed to a new environment, carrying a book with him to hide behind in uncomfortable situations, acting out when he felt out of control. The uncle understood coming from a background like his nephew's, where every change Jess had to go through as a kid had only made situations worse. He was still trying to teach the boy that change could also be a good thing.

"You're probably right," he agreed with the girl.

Rory nodded, "So anyway," she replied, raising her books, "I better get started on this."

"Sure, of course," he waved his hand, "Don't let me slow you down."

* * *

Luke knocked twice on Jess' door and waited until he heard the faintest 'yeah?' Before he let himself enter.

Jess was sitting at his desk, though it didn't seem he was doing anything particular other than staring off into space.

"I figured you couldn't get much work done without your books," Luke explained, placing Jess' abandoned bag from the living room onto his bed. "Sounds like you guys have quite a bit of work to do."

"Understatement," the teen sighed, turning to face the man. "It's going to take all night."

"Well you better get to it then," the uncle concluded with hopefulness.

Jess rolled his eyes and turned his back to the man once more, "I just got home. I need time to chill first."

Luke nodded like he expected the fight, "Which is why I waited a half hour before coming in here."

He knew Chilton wouldn't magically transform his nephew overnight, but a man could hope.

The boy sighed again, "It was a really long day uncle Luke. The kids sucked. The classes were intense. I'll get to it eventually, I promise."

Luke sighed in defeat, "Okay bud. I'm going to trust that you know what you're doing. If you get behind it's you who'll get in trouble from the school, not me."

Jess nodded his understanding, evidently prepared to take the consequences if need be.

"Suppers in an hour and I want you in bed by ten tonight so don't wait too long."

"Ten? I'm 15 you know," The boy scoffed.

"Exactly. A growing boy and it was a long day, which you are going to have to get up and do all over tomorrow. You'll thank me in the morning, trust me."

Jess rolled his eyes at the man's back as he left. He zeroed in on the bag now sitting on his bed full of books that he didn't have an ounce of motivation to open. He let out a long breath. It was going to be a long night.

* * *

 **A/N- This chapter has been ready for a while now, but it's been a rough few weeks for me and I wasn't able to give it that last read through until today. I hope you enjoyed the first Chilton installment! Let me know what you think! I may or may not be working on the first Friday night dinner scene as we speak... Please review if you can!**


	12. Chapter 12

September 8th

"You're still doing homework?" Rory asked the next day as she sat beside Jess on the bus, the older messily scribbling something into a workbook.

"Luke made me go to bed at ten last night," he informed as if that alone gave all the answers.

"I went to bed at ten too," she shrugged.

"Yeah and you spent the entire night since we got home doing homework. You realize we're never going to have a social life again, right?"

"You're being dramatic," she shook her head, "You heard the teachers, the first week's going to be intense because they want to make sure everyone's in the same place. The work's going to die down."

"That's what they _say_ ," his eyebrows rose though he was now smirking. Instead of elaborating he changed the subject. "I'm so looking forward to seeing Paris and Tristan today."

"Yeah, I'm looking forward to getting death glares and having to correct my name one million times."

"You know he's only doing that to bug you, he knows your name, just like he knows that my name's not 'Prep', which by the way, does not match my personality _at all._

Rory giggled, "You are probably the furthest thing from a prep at that school."

Jess shook his head thoughtfully, "How did my test scores even get around the school that fast?"

"I don't know, but for some strange reason I have a feeling Paris has something to do with it."

"She runs the school remember," Jess jested sarcastically causing Rory to laugh.

"How could I forget?"

* * *

The morning of day two was a lot easier than that of day one. Knowing where everything was being the main factor in things running a lot smoother. Jess already felt the weight from the day before lifting if not just slightly from his shoulders. Metaphorically speaking of course since the straps from his backpack still dug into his shoulders uncomfortably from the heavy textbooks he was carrying around. He would need to work through lunch if he planned to get enough work done during school to give himself any kind of a life once he got home. Working through lunch, he shook his head at the thought, who was he and where had Jess gone?

He exited second period with a game plan in mind. So far, he had an essay to write and six math questions to answer. Not so bad if each question didn't involve an a, b, c, d, e, and f. Still, he figured if he got the problems done during lunch, and the essay during study period, thus nixing what he usually dubbed 'reading period', he would probably only have an hour and a half of additional homework once he got home. It would still leave him enough time for a few games of basketball with Pete before curfew.

Just as he was getting excited at the prospect of free time, Jess was shaken from his thoughts as he turned and saw Paris cornering Rory down the hall. He rolled his eyes, 'what's this about now?', he thought to himself as he picked up his pace.

"I just wanted to make sure you weren't planning on going out for the school paper."

"Yeah," Rory pulled back the strap on her book bag and blinked with a dumb mock, "And I've already told you that I haven't decided yet. Right now all that's on my mind is getting through the first week."

"Everything okay here?" Jess knew his sister could stand her own, but that didn't stop him from putting himself between the two agitated girls.

"You know they only tell you the first week is the hardest so that small town transfers like you don't get overwhelmed. It's not going to be any easier by week two," Paris paid no attention to the new participant in their conversation. "I'd think long and hard about how much you can handle before committing to something and then backing out when you get buried in textbooks."

Whipping herself around, she took off down the hall.

"What was that all about?" an amused smirk danced on Jess' lips.

"Apparently Paris is threatened by me." A stray hair fell in front of her eye and she brushed it away as she walked, knowing Jess would follow.

"You're going to try out for the paper right? Telling Paris you didn't know, that was just getting her off your back?"

Rory's eyes averted as she shifted her books uncomfortably in her arms, "I don't know, I mean she has a point. What if it does get too much? Sure I was on the paper at Stars Hollow High, but I was also weeks ahead in my classes. Dropping an extracurricular halfway through the year doesn't look good to colleges."

"You won't need to drop it. She was just trying to scare you," His assuring brown eyes promised.

The look on her face was that of unconvinced, though after a pause she let a small smile pull at the corners of her mouth, "Why don't you join with me? We could keep each other motivated and hey two of us against one Paris couldn't hurt either!"

He was shaking his head before she got her whole speech out, completely certain that adding additional work to his pile would be a sure sign of insanity in anyone that wasn't Rory Gilmore.

"Oh come on Jess! I don't want to hear that it would be too much work because you just assured me that it wouldn't be!"

"Yeah, for you! Do I really look like the kind of guy who willingly does extra homework?"

"You're the kind of guy that's an amazing writer. C'mon Jess you can't deny that. You actively LIKE to write! It would be the perfect opportunity for you to get an extracurricular credit!"

She was getting excited now and if those begging puppy eyes weren't directed at him he would have teased her about it.

" _Rory._ "The warning had no fire behind it, but the irritation was dripping.

"Just say you'll think about it," she compromised, reaching her classroom and stopping before turning in.

He rolled his eyes as the bell rang, signalling he was late for his own class. "Fine, okay?"

She smiled wide, turning quickly into her room without another word. He shook his head as he jogged down the hall. He only said it to get her off his back for the time being, he told himself stubbornly.

* * *

September 10th

"Okay remember, small talk, nothing heavy, nothing controversial. They're going to twist our words no matter what we say, don't give them too many openings."

Jess wasn't sure if Lorelai was coaching them anymore, or instead having an inner battle of her own. He only knew that the days leading up to the first Friday night dinner had been tense and Lorelai had been in a downward spiral since the prior evening. He heard his aunt and uncle late into the night discussing her worries, Luke assuring and reassuring that nothing that happened there would, in fact, be the end of the world, yet Jess' stomach still swam with guilt as he listened to her concerns. She was doing this all for them, after all. It hit him as he listened to the woman confide her anxieties, somewhat dramatically, to her husband that she was sacrificing a great deal for her kids. Flipping his pillow to the cooler side and turning over, Jess had stubbornly lectured himself to appreciate his new school more from now on. He may have to put up with some things that he did not enjoy, but at least nobody was making him eat dinner with his mother every Friday night from now until forever. Yeah, that would definitely suck.

For that reason alone, Jess hadn't said a word as he was made to put on a suit directly after walking through the doors when he got home from school. Nor did he participate in the grandparent bashing that took place on the drive over, when even Rory had thrown a few complaints out. Instead, he had sat still in the car, quietly coaching himself to the fact that Luke was right, whatever happened in that house was not going to affect their day to day lives. They just needed to put up with whatever nonsense the elders threw at them every week and move on. If they didn't let it bug them then none of it would matter.

It was easier said than done. By the time the drinks were being ordered, he had already found the need to bite his tongue.

"Rory, Jess, what will you be drinking?" Emily began her hostess duties.

"Just a club soda, please," came Rory's mouse-like voice.

He felt the cold stare on him next, his fingers pressed tightly together, dancing through each other the only way he could relieve the nervous energy.

"Coke?"

"How about water?" she offered instead.

"Sounds perfect." His reply wasn't meant to sound sarcastic and he hoped it hadn't. He briefly wondered if the house really was void of soda or if Emily had been prepared to nix whatever his first choice would have been on principle alone.

By some gift from God, Jess hadn't been subjected to any direct questioning by either elder for the rest of the cocktail hour. He sat straight in his seat, feeling Rory shift every so often from the spot beside him. She hadn't been so lucky, unfortunately, though she also had a way of handling her grandparents that Jess didn't think he would ever learn.

By the time the maid's presence appeared in the room and it was announced that dinner was served, Jess graciously rose. They weren't out of the woods, but at least he would now have something to do with his hands which had become clammy and cold, the piece of skin next to the nail on his big thumb nearly stripped off absentmindedly. A nervous habit he could never seem to shake no matter how much Luke got on him about it.

"So, how are you enjoying your new school, Rory?" Richard allowed his plate to be set in front of him as he spoke.

"It's great. There's a lot of work so far, but we're keeping on top of it, right Jess?"

Nodding politely, Jess put a forkful of food in his mouth and began chewing. Another nervous habit that would allow him time for thought if any extra questioning came his way.

"Well, I know for a fact that Jess is having an excellent start to his year!" The way Emily's voice rose and her eyes bore into him with scorn made Jess squirm. He obviously wasn't the only one to notice the malicious tone as Lorelai was quick to jump in.

"What's that supposed to mean Mom?"

As if playing a game where she was now running the board she smiled when her bait was taken.

"Only that I had a late lunch with Hanlin Charleston the other day. He informed me that my 'grandson' had already gotten into a fight." Jess didn't know how she managed to make the word grandson sound like it had air quotes around it, but she had. He instantly felt everyone's eyes on him.

"Is there something you forgot to mention to us, Jess?" Luke asked curiously. Emily's word was not always reliable, but her facts were not usually pulled from thin air either.

"Tristan knocked his books out of his hand, Luke, Jess was just sticking up for himself," Rory defended.

"I shoved him once, that's it," Jess added, feeling uncomfortable.

"That was all he could do before Hanlin pulled them apart," Emily countered.

"He didn't pull us apart, we weren't even touching when Charleston got there," Jess' temper rose.

" _Principal_ Charleston, young man," Richard corrected, "I'm sure you know about Chilton's strict rules regarding conflict."

"Yeah the old bat informed me," the boy snapped.

" _Jess,"_ Luke scolded sharply.

"You see that is exactly the kind of behaviour we are talking about," Emily pointed her finger and Jess glared at it. "You have got to get a handle on that temper Lorelai. He's not going to get very far in life with behaviour like that."

"We know what we're doing _Mom_. If you two weren't ganging up on him every time he came over you would see that Jess is a very sweet boy. I'm sure if he felt the need to get physical at school, there must have been a very good reason."

Jess' cheeks reddened. He was fifteen being referred to as a 'sweet boy', but he appreciated his aunt sticking up for him.

"With all due respect Mrs. Gilmore how we parent Jess is between us and him and had we known about the fight we would have handled it, we _are_ going to handle it, whether it needs to be handled or not we will discuss. Jess is a good kid, and for now I think it's about time we changed the subject."

He and Lorelai had discussed the fact that now that they were indebted to the elders, they couldn't just storm out whenever things got tense like they used to do, but the uncle wasn't going to sit around and discuss the issue any longer either.

"Obviously it needed to be brought to your attention since he wasn't going to tell you about it himself, but I suppose now that you know we can be sure that the two of you will deal with the atrocious behaviour, we can let it go."

Rory shot Jess a sympathetic look from across the table, but he only returned it with an eye roll, assuring her that he was tougher than to let the words of the Gilmore's get him down.

* * *

"Seriously Jess, a fight?" Luke spoke as the car began to drive back to Stars Hollow.

"It wasn't really a fight," Rory piped up, "More of a small scuffle, right Jess?"

"Tristan was being a jerk, I made sure he knew I wasn't some timid new kid he could mess with, that's all," he explained. "Charleston walked by before anything even happened... Not that it would have of course."

"Of course," Luke agreed doubtfully. "Just make sure if it ever happens again, defending yourself, not starting a fight because that better not happen," he added on the side, "That you don't do it somewhere that any faculty who's on the ins with the Gilmores will see, okay?"

"Yeah Jess, small tip, it's better not to give the Gilmores any more ammo than they already have," Lorelai explained. "What may seem like a small infraction to you, is World War III to the Gilmores."

"Don't worry, I won't get in any more fights any time soon. I plan to steer clear of Tristan for the time being."

"I like that plan," Luke agreed. "It's only week one at this new school, I don't need any calls from the principal. Besides that Charleston guy scares me."

"Any friend of my parents scares me," Lorelai shuddered. "Well, otherwise, I think we made it out of our first 'Friday Night Dinner' unscathed, wouldn't you say?"

"It wasn't the worst dinner with the grandparents," agreed Rory.

"I mean, I know we made a pact not to bolt out at the first sign of trouble, but I was still 85% sure we would. That's progress friends!" Lorelai pumped her fist into the air in success.

"Now we've got a whole weekend free to laze around and do nothing," Jess smiled from the back.

Rory nodded, "I'm going to try to get the majority of my assignments done when we get home tonight so I can actually hang out with Lane for the first time in a week."

"Or, even better plan," Jess piped up, "All the assignments will still be there Sunday night and we can try to forget they exist for as long as possible."

"You are impossible, you know that right?" Rory shook her head, turning to the window.

"I've been told that a time or two... from every person in this car."

"Yeah? If you've noticed the theme have you ever thought about maybe working on that then?" Luke peered through the rearview mirror with a smirk.

Jess shook his head coolly, "Nah, imagine how dull your life would be without this charming personality!"

"It would definitely be less interesting," Lorelai agreed, trying to remember the eleven years before her now nephew came into the picture.

"I'd for sure have a lot less grey hairs," Luke added matter of factly.

"None of my books would be defaced!" Rory chimed in.

"Taylor wouldn't have our number on speed dial."

"Ok, ok, jeez, is it team up on Jess night? And you love it when I write in the margins so that's not a valid argument!" Jess pointed accusingly at his sister.

Lorelai let out a laugh, "Alright guys, let's give the poor boy a break. How about stopping for some ice-cream? Would that make our cranky boy happier?" she couldn't help tease once more.

Jess sighed, shaking his head and then with a small shrug, "...yes. Yes it would."

The rest of the car laughed loudly and Luke was soon pulling off the highway in search of a frozen dessert establishment that they could all agree on.

* * *

Later that night Jess was reading in bed, arm draped tiredly over his forehead and the words beginning to blur when he heard a knock and his uncle enter.

"Hey Bud, you reading or sleeping?"

"I just wanted to finish this chapter." He admitted, rubbing his eyes.

"Well Lorelai and I are heading up to bed, but I wanted to check in on you beforehand. Are you okay? I know it wasn't the best night, but it could have been worse, right?"

Jess sat up and placed his dog-eared book to the side, "I'm fine. Like Rory said, we've had worse nights at the Gilmore's."

Luke nodded slightly, "And about the fight-"

"I promise it really was no big deal Uncle Luke. It won't happen again. I've got it all under control," Jess cut him off before the man's worrying nature began to spiral.

"Okay, I'm going to let you handle it, it's just the last time-"

"Last time I was twelve Luke."

"Yeah and you were just adjusting to a new school back then too."

"I was a dumb kid."

"You weren't dumb-"

"I don't give in to peer pressure anymore. I'm not going to go out and steal a video game, you know I wouldn't do that, right?"

The uncle nodded thoughtfully. He did know. He was proud to say with a little help from himself and Lorelai, the kid really had grown up a lot. He had meant what he said at dinner, Jess was a good kid. He may have been misguided when he first came to Stars Hollow, but that good kid had always been there.

Luke smiled, "Okay. You're old enough to tell me that if you can handle it, then I will believe you. I just don't like anyone messing with my boy."

"Tristan has no real fight in him, he's just a jerk looking for attention, I've got it, seriously."

"Good. Now I think you should turn in too. It's Friday night so I'm not going to force you, but it didn't look like you were comprehending much of that book when I walked in here."

Jess nodded, "I'll just finish the last two pages."

Luke pulled Jess in for a side hug and then stood up with a stretch, "Goodnight Nephew. You know I love you, right?"

"Love you too."

* * *

 **A/N- I know I suck! I'm not even going to make excuses except here is a new chapter and the next will be posted eventually. Hope some of you are still here and you enjoy! Let me know if you do!**


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